Organosilicon compounds their preparation and their use

ABSTRACT

The invention relates to organosilicon compounds, and to the ways in which they can be made and used.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application claims priority under 35 U.S.C. § 119 to Germanapplication 10 2005 038 791.8, filed on Aug. 17, 2005, the contents ofwhich is incorporated by reference in its entirety.

FIELD OF THE INVENTION

The present invention is directed to organosilicon compounds, theirpreparation and their use.

BACKGROUND OF THE INVENTION

The synthesis of

-   CH₃—C(O)—S—CH₂—Si(O—CH₂—CH₂) ₃N,-   CH₃—C(O)—S—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and-   CH₃—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N    by transesterification of the corresponding methoxy- and    ethoxysilanes with triethanolamine with liberation of methanol or    ethanol is known from J. Gen. Chem. USSR (EN) 45, 1975, 1367    (Voronkov et al.).

U.S. Pat. No. 4,048,206 discloses the synthesis of a compound of thegeneral formula X′-Z′-Si(OR′)₃N, where X′may be R″C(O)M′, M′ may be S,R″ may be alkyl, Z′ may be a bivalent hydrocarbon and R′ may be—CH₂—CH₂— or —CH(CH₃)—CH₂—. These compounds can be used, inter alia, asan additive for synthetic polymers.

In addition, the synthesis of

-   R′—S—CH₂—CH₂—Si(O—CH(CH₃) CH₂)_(m′)(O—CH₂—CH₂)_(3−m′)N by a    photochemically supported addition reaction of R′SH with    CH₂═CH—Si(O—CH(CH₃)CH₂)_(m′)(O—CH₂—CH₂)_(3−m′)N is known from J.    Gen. Chem. USSR (EN) 49, 1979, 1130-1136 (Voronkov et al.).

Compounds of the formulaR′—S—(CH₂)_(n′)Si(O—CH(CH₃)CH₂)_(3−-m′)(O—CH₂—CH₂)_(m′)N are known fromJ. Gen. Chem. USSR (EN), 49, 1979, 529-536.

The synthesis of compounds of the formulae

-   CH₃—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   EtO—C(S)—S—CH₂—Si(O—CH₂—CH₂)₃N and-   Et₂N—C(S)—S—CH₂—Si(O—CH₂—CH₂)₃N    from the alkali metal salts CH₃C(O)S—K, EtO—C(S)—S—K and    Et₂N—C(S)—S—Na in o-xylene or DMF is known from J. Gen. Chem. USSR    (EN) 69(3), 1999, 394-398 (Sorokin et al.).

Furthermore, the synthesis of (R′O)₂P(S)SCH₂Si(OCH₂CH₂)₃N and(R′O)₂P(S)S(CH₂)₃Si(OCH₂CH₂)₃N is known from Bull. Acad. Sci. USSR Div.Chem. Sci. (EN), 36, 8, 1987, 1745-1747 (Voronkov et al.).

One disadvantage of the known compounds concerns their processingbehaviour in rubber mixtures, especially at high mixture viscosities.

DESCRIPTION OF THE INVENTION

It is an object of the invention to provide organosilicon compoundswhich cannot release volatile alcohols during the binding to the filler,at the same time have a high reactivity to filler and polymer and resultin improved processability, for example a low viscosity of the mixture,good extrusion behaviour, good flowability, an appropriate Mooney scorchtime or an improved incubation time, and/or improved dynamic propertiesin rubber mixtures. The invention relates to organosilicon compounds ofthe general formula (I),Q—[S—G—Si(—O—CX¹X²—CX¹X³—)₃N]  (I)in which Q is

-   six_(3−t) ⁴X_(t−) ⁵, where t ═0, 1 or 2,-   Y—(═O)—Z—C(═O)—, Y—C(═S)—Z—C(═S)—, Y—C(═NR)—Z—C(═NR)—, Y—C(═O)—,    Y—C(═S)—, Y—C(═NR)—, Y-S(═O)—, Y—S(═O)₂—, (X⁶)(x⁷)P(═S)—,    (X⁶)(X⁷)P(═O)—, X⁸—C(═O)—, R—C(═S)—, R—C(═NR)—, R—S—C(═NR)—,    R—S—C(═O)—, R—S—C(═S)—, (X⁹)₂N—C(═O)—, (X⁹)₂N—C(═S)—, R—NR—C(═NR)—,    (X⁸)₂N—C(═O)—, (X⁸)₂N—C(═S)—, (X⁸)HN—C(═O)—, (X⁸)NH—C(═S)—,    R—O—C(═O)—, X⁹—O—C(═S)—, R—O—C(═NR)—, R—S(═O)—, R—S(═O)₂—,    R—O—S(═O)₂—, R—NR—S(═O)₂—, R—S—S(═O)₂—, R—S—S(═O)—, R—O—S(═O)—,    R—NR—S(═O)—, (R—S—)₂P(═O)—, (R—S—)₂P(═S)—, (R—NR—)₂P(═S)—,    (R—NR—)₂P(═O)—, R—(R—S—)P(═O—, R—(R—O—)P(═O)—, R—(R—S—)P(═S)—,    R—(R—O—)P(═S)—, R—(R—NR—)P(═O)—, R—(R—NR—)P(═S)—,    R—NR—)(R—S—)P(═O)—, (R—O—)(R—NR—)P(═O)—, (R—O—)(R—S—)P(═O)—,    (R—O—)(R—S—)P(═S)—, (R—NR—)(R—S—)P(═S)—, (R—O—)(R—NR—)P(═S)—,    (R—O—)(Y)P(═O)—, (R—O—)(Y)P(═S)—, (R—S—)(Y)P(═O)—, (R—S—)(Y)P(═S)—,    (R—NR—)(Y)P(═O)—, (R—NR—)(Y)P(═S)—, R—(Y)P(═O)—, R—(Y)P(═S)—,    Y₂P(═O)—, Y₂P(═S)—or Y₂P(NR)—,-   R are identical or different and are hydrogen (H), a straight-chain,    cyclic or branched, substituted or unsubstituted, saturated or    unsaturated monovalent (C₁-C₂₄)—, preferably (C₃-C₂₄)—, particularly    preferably (C₅-C₁₈—, very particularly preferably (C₈-C₁₈)—,    hydrocarbon chain, an unsubstituted or —NH2, HS—, Cl— or    Br-substituted (C₆-C₂₄)—, preferably (C₁₀-C₂₄)—, particularly    preferably (C₁₄-C₂₄)—, aryl group or an unsubstituted or —NH₂, HS—,    Cl—or Br-substituted (C₇-C₂₄)—, preferably (C₉-C₂₄)—, particularly    preferably (C₁₂-C₂₄)—, aralkyl group,-   Y are identical or different and are:-   [—S—G—Si(—O—CX¹X²—CX¹X³—)₃N],-   G are identical or different and when Q is C₆H₅—C(═O)— G is a    straight-chain, cyclic or branched, substituted or unsubstituted,    saturated or unsaturated divalent (C₃-C₃₀)—, preferably (C₃-C₂₄)—,    particularly preferably C₃— or (C₅-C₂₀)—, very particularly    preferably C₃— or (C₆-C₁₈)—, exceptionally preferably C₃— or    (C₇-C₁₈)—, hydrocarbon chain; optionally, the hydrocarbon chains may    contain unsaturated moieties, such as double bonds and/or triple    bonds or alkylaromatics (aralkyl) or aromatics, or may be    substituted by them; the substituted hydrocarbon chains can    preferably be substituted by halogen, for example Cl or Br, —OOR or    HS—,    and for all other Q G is a straight-chain, cyclic or branched,    substituted or unsubstituted, saturated or unsaturated divalent    (C₁-C₃₀)—, preferably (C₂-C₂₄)—, particularly preferably (C₃-C₂₀)—,    very particularly preferably C₃— or (C₅-C₁₈)—, exceptionally    preferably C₃— or (C₆-C₁₈)—, hydrocarbon chain; optionally, the    hydrocarbon chains may contain unsaturated moieties, such as double    bonds and/or triple bonds or alkylaromatics (aralkyl) or aromatics,    or may be substituted by them; the substituted hydrocarbon chains    can preferably be substituted by halogen, for example Cl or Br, —OOR    or HS—,-   Z is a straight-chain, cyclic or branched, substituted or    unsubstituted, saturated or unsaturated divalent (C₁-C₂₄)—,    preferably (C₂-C₂₄)—, particularly preferably (C₄-C₂₀)—, very    particularly preferably (C₆-C₁₈)—, exceptionally preferably    (C₁₀-C₁₈)—, hydrocarbon chain; optionally, the hydrocarbon chains    may contain unsaturated moieties, such as double bonds and/or triple    bonds or alkylaromatics (aralkyl) or aromatics or may be substituted    by them; the substituted hydrocarbon chains can preferably be    substituted by halogen, for example Cl or Br, —OOR or HS—, or is a    divalent, aliphatic or aromatic, saturated or unsaturated    hydrocarbon chain functionalized with at least two NH groups, for    example —NH—-   T¹ —NH— or —NH—T¹—CH₂—T²—NH—, where T¹ and T² may be identical or    different and may be a divalent hydrocarbon chain, aromatic or    alkylaromatic, optionally substituted by —l, —Br, —NH2, —NO₂,    —O—alkyl (C₁-C₁₀) or methyl,-   X¹, X² and X³, in each case independently of one another, denote    hydrogen (—H), (C₁-C₁₆)-alkyl, preferably (C₁-C₈)-alkyl,    particularly preferably methyl or ethyl, or aryl, preferably phenyl,-   X⁴ and X⁵, in each case independently of one another, denote    hydrogen (—H), a straight-chain, cyclic or branched, substituted or    unsubstituted, saturated or unsaturated monovalent (C₁-C₂₄)—,    preferably (C₄-C₂₀)—, very particularly preferably (C8-C₂₀)—,    hydrocarbon chain, exceptionally preferably methyl, ethyl, butyl,    C₈-alkyl, C₁₆-alkyl or C₁₈-alkyl, a (C₁-C₁₈)-alkoxy group,    preferably methoxy, ethoxy, propoxy, C₈-alkoxy, C₁₂-alkoxy,    C₁₆-alkoxy or C₁₈-alkoxy, an aryl group, preferably phenyl, an    alkylether group O—(CR₂ ^(I)-CR₂ ^(I)) —O—Alk or alkylpolyether    group O—(CR₂ ^(I)-CR₂ ^(I))_(y)—Alk, where y=2-25, preferably    y=2-15, particularly preferably y=3-10, very particularly preferably    y=3-6, and RI, independently of one another, are H or an alkyl    group, preferably a CH₃ group, Alk is a linear or branched,    saturated or unsaturated alkyl chain having 1-30 carbon atoms    (C₁-C₃₀), preferably C₁-C₂₀, particularly preferably C₄-C₁₈, very    particularly preferably C₈-C₁₆,an aralkyl group, preferably    —CH₂—CH₂-phenyl, a halogen, preferably F—, Cl— or Br—, a radical    Alk—(COO), preferably acetoxy, C₁₁H₂₃(COO), C₁₃H₂₇ (COO), C₁₅H₃₁    (COO) or C₁₇H₃₅ (COO),    or Y, preferably [—S—CH₂—Si(—O—CH₂—CH₂—)₃N],-   [—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N],-   [—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N],-   [—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N],-   [—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N],-   [—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]-   [—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N],-   [—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N],-   [—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N] or-   [—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N],-   X⁶ and X⁷, in each case independently of one another, denote    hydrogen (—H), —OH, —SH, a straight-chain, cyclic or branched,    substituted or unsubstituted, saturated or unsaturated monovalent    (C₁-C₂₄)—, preferably (C₃-C₂₀)—, particularly preferably (C₆-C₂₀)—,    very particularly preferably (C₈-C₂₀)—, hydrocarbon chain,    exceptionally preferably methyl, ethyl, n-propyl, isopropyl,    n-butyl, tert-butyl, C₆-alkyl, C₆-cycloalkyl, C₈-alkyl, C₁₆-alkyl or    C₁₈-alkyl, a (C₄—₂₄)-alkoxy group, preferably (C₆—₂₄) alkoxy,    particularly preferably (C₈-C₂₄) alkoxy, very particularly    preferably (C₁₀-C₈) alkoxy, exceptionally preferably C₆-alkoxy,    C₆-cycloalkoxy, C₈-alkoxy, C₁₂-alkoxy, C₁₆-alkoxy or C₁₈-alkoxy, an    aryl group, preferably phenyl, an alkylether group O—(CR₂ ^(I)- CR₂    ^(I))—O—Alk or alkylpolyether group O—-(CR₂ ^(I)-CR₂O)_(y)—Alk, an    aralkyl group, preferably —CH₂—CH₂—phenyl, a halogen, preferably F—,    Cl— or Br—, or a radical Alk—(COO), preferably acetoxy, C₁₁H₂₃(COO),    C₁₃H₂₇(COO), C₁₅H₃₁(COO) or C₁₇H₃₅(COO),-   X⁸ are identical or different and denote hydrogen (H), a    straight-chain, cyclic or branched, substituted or unsubstituted,    saturated or unsaturated monovalent (C₂-C₂₄)—, preferably (C₇-C₂₄)—,    particularly preferably C₇— or (C₉-C₁₉)—, exceptionally preferably    C₇— or (C₁₁-C₁₇)—, hydrocarbon chain, a substituted, preferably    —NH₂—, HS—, Cl—, Br—, O-alkyl-, —NCO— or —NCS-substituted,    (C₆-C₂₄)—, preferably (C₁₀-C₂₄)—, particularly preferably    (C₁₄-C₂₄)—, aryl group, an unsubstituted (C₆-C₂₄)—, preferably    (C₁₀-C₂₄)—, particularly preferably (C₁₄-C₂₄)—, aryl group or an    unsubstituted or substituted, preferably —NH₂—, HS—, Cl—, Br—,    O-alkyl, —NCO— or —NCS-substituted, (C₇-C₂₄)—, preferably (C₉-C₂₄)—,    particularly preferably (C₁₂-C₂₄)—, aralkyl group,-   X are identical or different and denote hydrogen (H), a    straight-chain, cyclic or branched, substituted or unsubstituted,    saturated or unsaturated monovalent (C4-C₂₄)—, preferably (C₆-C₂₄)—,    particularly preferably (C₇-C₁₈)—, exceptionally preferably    (C₉-C₁₆)—, hydrocarbon chain, a substituted, preferably —NH₂—, HS—,    Cl—, Br—, O-alkyl-, —NCO— or —NCS-substituted, (C₆-C₂₄)—, preferably    (C₁₀-C₂₄)—, particularly preferably (C₁₄-C₂₄)—, aryl group, an    unsubstituted (C₇-C₂₄)—, preferably (C₁₀-C₂₄)—, particularly    preferably (C₁₄-C₂₄)—, aryl group or an unsubstituted or    substituted, preferably —NH₂—, HS—, Cl—, Br—, O-alkyl, —NCO— or    —NCS-substituted, (C₇-C₂₄)—, preferably (C₉-C₂₄)—, particularly    preferably (C₁₂-C₂₄)—, aralkyl group.

R can preferably be methyl, ethyl, propyl, butyl or cyclohexyl, C₇H₁₅,C₉H₁₉, C₁₁H₂₃, C₁₃H₂₇, C₁₅H₃₁, phenyl, p-tolyl, o-tolyl or m-tolylgroup. The substituted hydrocarbon groups R may be substituted byhalogen, —COOR or HS—.

G can preferably be —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂—,—CH(CH₃)—, —CH₂CH(CH₃)—, —CH(CH₃)CH₂—, —C(CH₃)₂—, —CH(C₂CH₅)—,—CH₂CH₂CH(CH₃)—, —CH(CH₃)—CH₂CH₂—, —CH₂CH(CH₃)CH₂—,—CH₂—C₆H₄—CH₂——CH₂—C₆H₄—CH₂—CH₂— or —CH₂—CH₂-C₆H₄—CH₂—CH₂—.

Z can preferably be —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH₂CH₂CH_(CH) ₂—,—CH₂CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂CH₂CH₂CH₂—, —CH(CH₃)—, —CH₂CH(CH₃)—,—CH(CH₃)CH₂—, —C(CH₃)₂—, —CH(C₂H₅)—, —CH₂CH₂CH(CH₃)—, —CH(CH₃)—CH₂CH₂—,—CH₂CH(CH₃)CH₂—, —C₄H₈—, —C₆H₁₂—, —C₈H₁₆—, —C₁₀H₂₀—, —C₁₂H₂₄—, —C₆H₄—,—CH₂—C₆H₄—CH₂—, —CH₂—C₆H₄—CH₂—CH₂—, —CH₂CH₂—C₆H₄—CH₂—CH₂—,—NH—(CH₂)₂—NH—, —NH—(CH₂)₃—NH—, —NH—(CH₂)₄—NH—, —NH—(CH₂)₅—NH—,—NH—(CH₂)₆—NH—, —NH—(CH₂)₇—NH—, —NH—(CH₂)₈—NH—, —NH—(CH₂)₉—NH—,—NH—(CH₂)₁₀—NH—, —NH—(CH₂)₁₁—NH—, —NH—(CH₂)₁₂—NH—,

-   X⁴ and X⁵ can preferably be a methyl, ethyl, propyl, butyl or    cyclohexyl, C₇H₁₅, C₈H₁₇, C₉H₁₉, C₁₁H₂₃, C₁₃H₂₇, C₁₅H₃₁, C₁₆H₃₃,    phenyl, p-tolyl, o-tolyl or m-tolyl group.-   x⁸ can preferably be propyl, butyl or cyclohexyl, C₇H15, C₈H₁₇,    C₉H₁₉, C₁₁H₂₃, C₁₃H₂₇, C₁₅H₃₁, C₁₇H₃₅, phenyl, p-tolyl, o-tolyl or    m-tolyl group. The substituted hydrocarbon chains x⁸ may be    substituted by halogen, —OOR or HS—.-   X⁹ can preferably be propyl, butyl or cyclohexyl, C₇H₁₅, C₉H₁₉,    C₁₁H₂₃, C₁₃H₂₇, C₁₅H₃₁, p-tolyl, o-tolyl or m-tolyl group. The    substituted hydrocarbon chains X⁹ may be substituted by halogen,    —OOR or HS—.

The following substituted aryl groups and aralkyl groups areparticularly preferred for X⁸ and X⁹:

Organosilicon compounds of the general formula (I) may be mixtures oforganosilicon compounds of the general formulae (I). Organosiliconcompounds of the general formula (I) may be hydrolysis products of theorganosilicon compounds of the general formula (I).

Organosilicon compounds of the general formula (I) where Q is X⁸—C(═O)—may be:

-   C₅H₁₁—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   phenyl-C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   phenyl-C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   phenyl-C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₅H₁₁—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₇H₃₅—C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   phenyl-C(O)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   phenyl-C(O)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N or-   phenyl-C(O)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N.

Organosilicon compounds of the general formula (I) may be:

-   Me₃Si—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   Me₃Si—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   Me₃Si—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   Me₃Si—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   Me₃Si—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   Me₂Si—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₂,-   Me₂Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₂,-   MeSi—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   MeSi—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N]₃,-   Me₃Si—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   Me₃Si—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   Me₃Si—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   Me₃Si—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   Me₃Si—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   Me₂Si—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₂,-   Me₂Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₂,-   Me₂Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₂,-   MeSi—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   MeSi—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   MeSi—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₃H₇Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₄H₉Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₈H₁₇Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃,-   C₁₆H₃₃Si—[S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃ or-   C₁₆H₃₃Si—[S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N]₃.

Organosilicon compounds of the general formula (I) where Q is(X⁸)₂N—C(═O)— and M′═S or O may be:

-   C₃H₇NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₇NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₇NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₇NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₇NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₅NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₅NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₅NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₅NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₃H₅NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   PhenylNH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   PhenylNH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   PhenylNH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₄H₉NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₇H₁₅NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₉H₁₉NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₁H₂₃NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₃H₂₇NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   C₁₅H₃₁NH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   PhenylNH—C(M′)—S—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   PhenylNH—C(M′)—S—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N or-   PhenylNH—C(M′)—S—CH(CH₃)—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N.

Organosilicon compounds of the general formula (I) where Q isY—C(═M′)—Z—C(C═M′)— and M′═S or O may be:

-   N(—CH₂—CH₂—O—)₃Si—CH₂—S—C(M′)—NH—(ortho)C₆H₄—NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—CH₂—S—C(M′)—NH—(meta)C₆H₄—NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—CH₂—S—C(M′)—NH—(para)C₆H₄—NH—C(M′)—S—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₂—S—C(M′)—NH—(ortho)C₆H₄—NH—C(M′)—S—(CH₂)₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₂—S—C(M′)—NH—(meta)C₆H₄—NH—C(M′)—S—(CH₂)₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₂—S—C(M′)—NH—(para)C₆H₄—NH—C(M′)—S—(CH₂)₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—NH—(ortho)C₆H₄—NH—C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—NH—(meta)C₆H₄—NH—C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—NH—(para)C₆H₄—NH—C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—    —C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—    —C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N,-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—    —C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N or-   N(—CH₂—CH₂—O—)₃Si—(CH₂)₃—S—C(M′)—    —C(M′)—S—(CH₂)₃—Si(—O—CH(CH₃)—CH₂—)₃N.

Organosilicon compounds of the general formula (I) may furthermore be:

-   N(CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₂H₄—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₂—S—C(O)—C₂H₄—C(O)—S—(CH₂)₂—Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₃—S—C(O)—C₂H₄—C(O)—S—(CH₂)₃—Si(OCH₂CH₂)₃N,-   N (CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₄H₈—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₂—S—C(O)—C₄H₈—C(O)—S—(CH₂)₂—Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₃—S—C(O)—C₄H₈—C(O)—S—(CH₂)₃—Si(OCH₂CH₂)₃N,-   N(CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₆H₁₂—C(O) —S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₂—S—C(O)—C₆H₁₂—C(O)—S—(CH₂)₂—Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₃—S—C(O)—C₆H₁₂—C(O)—S—(CH₂)₃—Si(OCH₂CH₂)₃N,-   N(CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₈H₁₆—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₂—S—C(O)—C₈H₁₆—C(O)—S—(CH₂)₂—Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si—(CH₂)₃—S—C(O)—C₈H₁₆—C(O)—S—(CH₂)₃—Si(OCH₂CH₂)₃N,-   N(CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₁₀H₂₀—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si(CH₂)₂—S—C(O)—C₁₀H₂₀—C(O)—S—(CH₂)₂Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si(CH₂)₃—S—C(O)—C₁₀H₂₀—C(O)—S—(CH₂)₃Si(OCH₂CH₂)₃N,-   N(CH₂—CH₂—O)₃Si—CH₂—S—C(O)—C₆H₄—C(O)—S—CH₂—Si(O—CH₂—CH₂)₃N,-   N(CH₂CH₂O)₃Si(CH₂)₂—S—C(O)—C₆H₄—C(O)—S—(CH₂)₂Si(OCH₂CH₂)₃N,-   N(CH₂CH₂O)₃Si(CH₂)₃—S—C(O)—C₆H₄—C(O)—S—(CH₂)₃Si(OCH₂CH₂)₃N,-   N(CH₂CH (CH₃)O)₃SiCH₂—S—C(O)—C₂H₄—C(O)—S—CH₂Si(OCH (CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₂H₄—C(O)—S—(CH₂)₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₂H₄—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃SiCH₂—S—C(O)—C₄H₈—C(O)—S—CH₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₄H₈—C(O)—S—(CH₂)₂Si(OCH (CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₄H₈—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃SiCH₂—S—C(O)—C₆H₁₂—C(O)—S—CH₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₆H₁₂—C(O)—S—(CH₂)₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₆H₁₂—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N,N(CH₂CH(CH₃)O)₃SiCH₂—S—C(O)—C₈H₁₆C(O)—S—CH₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₈H₁₆—C(O)—S—(CH₂)₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₈H₁₆—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃SiCH₂—S—C(O)—C₁₀H₂₀—C(O)—S—CH₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₁₀H₂₀—C(O)—S—(CH₂)₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₁₀H₂₀—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃SiCH₂—S—C(O)—C₆H₄—C(O)—S—CH₂Si(OCH(CH₃)CH₂)₃N,-   N(CH₂CH(CH₃)O)₃Si(CH₂)₂—S—C(O)—C₆H₄—C(O)—S—(CH₂)₂Si(OCH(CH₃)CH₂)₃N    or-   N(CH₂CH(CH₃)O)₃Si(CH₂)₃—S—C(O)—C₆H₄—C(O)—S—(CH₂)₃Si(OCH(CH₃)CH₂)₃N.

The invention furthermore relates to a process for the preparation ofthe organosilicon compounds according to the invention, which ischaracterized in that at least one organosilicon compound of the generalformula (II)X¹⁰[S—G—Si(—O—CX¹X²—CX¹X³—)₃N]  (II)in which G, X¹, X² and X³ have the above mentioned meanings and X¹⁰ isH, alkali metal, for example Li, Na or K, alkaline earth metal orammonium cation, for example alkylammonium cation, dialkylammoniumcation, trialkylammonium cation or tetraalkylammonium cation, is reactedwith at least one organic or inorganic acid anhydride, one organic orinorganic acid halide or organic or inorganic ester selected from thegroup consisting of

-   Y—C(═O)—O—C(═O)—Y, Y—C(═S)—O—C(═S)—Y, Y—C(═NR)—O—C(═NR)—Y,    Y—C(═O)—S—C(═O)—Y, Y—C(═S)—S—C(═S)—Y, Y—C(═NR)—S—C(═NR)—Y,    Y—S(═O)—O—S(═O)—Y, Y—S(═O)₂—O—S(═O)₂—Y, X⁸—C(═O)—O—C(═O)—X⁸,    X⁸—C(═O)—S—C(═O)—X⁸, R—C(═S)—O—C(═O)—R, R—C(═S)—S—C(═O)—R,    R—S—C(═O)—O—C(═O)—S—R, R—S—C(═O)—S—C(═O)—S—R, R—S—C(═S)—O—C(═S)—S—R,    R—S—C(═S)—S—C(═S)—S—R, R—O—C(═O)—O—C(═O)—OR, R—O—C(═O)—S—C(═O)—OR,    R—O—C(═S)—O—C(═S)—OR, R—O—C(═S)—S—C(═S)—OR, R—S(═O)—O—S(═O)—R,    R—S(═O)—S—S(═O)—R, R—O—S(═O)—O—S(═O)—O—R, R—O—S(═O)—S—S(═O)—O—R,    R—O—S(═S)—O—S(═S)—O—R, R—O—S(═S)—S—S(═S)—O—R, R—S—S(═O)—O—S(═O)—S—R,    R—S—S(═O)—S—S(═O)—S—R, R—S—S(═S)—O—S(═S)—S—R, R—S—S(═S)—S—S(═S)—S—R,    R—S(═O)₂—O—S(═O)₂—R, R—S(═O)₂—S—S(═O)₂—R, R—S(═S)₂—O—S(═S)₂—R,    R—S(═S)₂—S—S(═S)₂—R, R—O—S(═O)₂—O—S(═O)₂—O—R,    R—O—S(═O)₂—S—S(═O)₂—O—R, R—O—S(═S)₂—O—S(═S)₂—O—R,    R—O—S(═S)₂—S—S(═S)₂—O—R, R—S—S(═O)₂—O—S(═O)₂—S—R,    R—S—S(═O)₂—S—S(═O)₂—S—R, R—S—S(═S)₂—O—S(═S)₂—S—R,    R—S—S(═S)₂—S—S(═S)₂—S—R,-   SiX⁴ _(s)X⁵ _(2−s)(Y)—S—SiX⁴ _(s)X⁵ _(2−s)(Y), Six⁴ _(3−t)X⁵    _(t)—S—Six⁴ _(3−t)X⁵ _(t), Y₂SiX⁴—S—SiX⁵Y₂, Y₂P(═O)—S—P(═O)Y₂,    Y₂P(═S)—S—P(═S)Y₂,-   SiX⁴ _(3−t)X⁵ _(t)-halogen, halogen-C(═O)—Z—C(═O)-halogen,    halogen-C(═S)—Z—C(═S)-halogen, halogen-C(═NR)—Z—C(═NR)-halogen,    Y—C(═O)—Z—C(═O)-halogen, Y—C(═S)—Z—C(═S)-halogen,    Y—C(═NR)—Z—C(═NR)-halogen, halogen-C(═O)-halogen,    halogen-C(═S)-halogen, halogen-C(═NR)-halogen,    halogen-S(═O)-halogen, halogen-S(═O)₂-halogen, Y—C(═O)-halogen,    Y—C(═S)-halogen, Y—C(═NR)-halogen, Y—S(═O)-halogen,    Y—S(═O)₂-halogen, (X⁶)(X⁷)P(═S)-halogen, (X⁶)(X⁷)P(═O)-halogen,    X⁸—C(═O)-halogen, R—C(═S)-halogen, R—C(═NR)-halogen,    R—S—C(═NR)-halogen, R—S—C(═O)-halogen, R—S—C(═S)-halogen,    (X⁹)₂N—C(═O)-halogen, (X⁹)₂N—C(═S)-halogen, R—NR—C(═NR)-halogen,    R—O—C(═O)-halogen, X⁹—O—C(═S)-halogen, R—O—C(═NR)-halogen,    R—S(═O)-halogen, R—S(═O)₂-halogen, R—O—S(═O)₂-halogen,    R—NR—S(═O)₂-halogen, R—S—S(═O)₂-halogen, R—S—S(═O)-halogen,    R—O—S(═O)-halogen, R—NR—S(═O)-halogen, (R—S—)₂P(═O)-halogen,    (R—S—)₂P(═S)-halogen, (R—NR—)₂P(═S)-halogen, (R—NR—)₂P(═O)-halogen,    R—(R—S—)P(═O)-halogen, R—(R—O—)P(═O)-halogen, R—(R—S—)P(═S)-halogen,    R—(R—O—)P(═S)-halogen, R—(R—NR—)P(═O)-halogen,    R—(R—NR—)P(═S)-halogen, (R—NR—)(R—S—)P(═O)-halogen,    (R—O—)(R—NR—)P(═O)-halogen, (R—O—)(R—S—)P(═O)-halogen,    (R—O—)(R—S—)P(═S)-halogen, (R—NR—)(R—S—)P(═S)-halogen,    (R—O—)(R—NR—)P(═S)-halogen, (R—O—)P(═O)(O—R)₂, (R—O—)P(═S)(O—R)₂,    (R—S—)P(═O)(O—R)₂, (R—S—)P(═S)(O—R)₂, (R—NR—)P(═O)(O—R)₂,    (R—NR—)P(═S)(O—R)₂, R—P(═O)(O—R)₂, R—P(═S)(O—R)₂,    (R—O—)(Y)P(═O)-halogen, (R—O—)(Y)P(═S)-halogen,    (R—S—)(Y)P(═O)-halogen, (R—S—)(Y)P(═S)-halogen,    (R—NR—)(Y)P(═O)-halogen, (R—NR—)(Y)P(═S)-halogen,    R—(Y)P(═O)-halogen, R—(Y)P(═S)-halogen, P(═O)(halogen)₃,    P(═S)(halogen)₃, P(NR)(halogen)₃, Y—P (═O)(halogen)₂,    Y—P(═S)(halogen)₂, Y—P(NR)(halogen)₂, Y₂P(═O)-halogen,    Y₂P(═S)-halogen, Y₂P(NR)-halogen,-   SiX⁴ _(3−t)X⁵ _(t)—O—R, SiX⁴ ₂—(O—R)₂, SiX⁵—(O—R)₃,    R—O—C(═O)—Z—C(═O)—O—R, R—O—C(═S)—Z—C(═S)—O—R,    R—O—C(═NR)—Z—C(═NR)—O—R, halogen-C(═O)—Z—C(═O)—O—R,    halogen-C(═S)—Z—C(═S)—O—R, halogen-C(═NR)—Z—C(═NR)—O—R,    R—O—C(═O)—Z—C(═O)—O—R, R—O—C(═S)—Z—C(═S)—O—R,    R—O—C(═NR)—Z—C(═NR)—O—R, Y—C(═O)—Z—C(═O)—O—R, Y—C(═S)—Z—C(═S)—O—R,    Y—C(═NR)—Z—C(═NR)—O—R, halogen-C(═O)—O—R, halogen-C(═S)—O—R,    halogen-C(═NR)—O—R, halogen-S(═O)—O—R, halogen-S(═O)₂—O—R,    R—O—C(═O)—O—R, R—O—C(═S)—O—R, R—O—C(═NR)—O—R, R—O—S(═O)—O—R,    R—O—S(═O)₂—O—R, Y—C(═O)—O—R, Y—C(═S)—O—R, Y—C(═NR)—O—R, Y—S(═O)—O—R,    Y—S(═O)₂—O—R, (X⁶)(X⁷)P(═S)—O—R, (X⁶)(X⁷)P(═O)—O—R, X⁸—C(═O)—O—R,    R—C(═S)—O—R, R—C(═NR)—O—R, R—S—C(═NR)—O—R, R—S—C(═O)—O—R,    R—S—C(═S)—O—R, (X⁹)₂N—C(═O)—O—R, (X⁹)₂N—C(═S)—O—R, R—NR—C(═NR)—O—R,    X⁹—O—C(═S)—O—R, R—S(═O)—O—R, R—S(═O)₂—O—R, R—NR—S(═O)₂—O—R,    R—S—S(═O)₂—O—R, R—S—S(═O)—O—R, R—NR—S(═O)—O—R, (R—NR—)₂P(═S)—O—R,    (R—NR—)₂P(═O)—O—R, R—(R—S—)P(═O)—O—R, R—(R—S—)P(═S)—O—R,    R—(R—NR—)P(═O)—O—R, R—(R—NR—)P(═S)—O—R, (R—NR—)(R—S—)P(═O)—O—R,    (R—O—)(R—NR—)P(═O)—O—R, (R—NR—)(R—S—)P(═S)—O—R, (R—S—)P(═O)(O—R)₂,    (R—S—)P(═S)(O—R)₂, (R—NR—)P(═O)(O—R)₂, (R—NR—)P(═S)(O—R)₂,    R—P(═O)(O—R)₂, R—P(═S)(O—R)₂, (R—S—)(Y)P(═O)—O—R,    (R—S—)(Y)P(═S)—O—R, (R—NR—)(Y)P(═O)—O—R, (R—NR—)(Y)P(═S)—O—R,    R—(Y)P(═O)—O—R, R—(Y)P(═S)—O—R, P(═O)(O—R)₃, P(═S)(O—R)₃,    P(NR)(O—R)₃, Y—P(═O)(O—R)₂, Y—P(═S)(O—R)₂, Y—P(NR)(O—R)₂,    Y₂P(═O)—O—R, Y₂P(═S)—O—R or Y₂P(NR)—O—R, SiX⁴ _(3−t)X⁵ _(t)—S—R,    SiX⁴ ₂—(S—R)₂, SiX⁵—(S—R)₃, R—O—C(═O)—Z—C(═O)—S—R,    R—O—C(═S)—Z—C(═S)—S—R, R—O—C(═NR)—Z—C(═NR)—S—R,    halogen-C(═O)—Z—C(═O)—S—R, halogen-C(═S)—Z—C(═S)—S—R,    halogen-C(═NR)—Z—C(═NR)—S—R, R—S—C(═O)—Z—C(═O)—S—R,    R—S—C(═S)—Z—C(═S)—S—R, R—S—C(═NR)—Z—C(═NR)—S—R, Y—C(═O)—Z—C(═O)—S—R,    Y—C(═S)—Z—C(═S)—S—R, Y—C(═NR)—Z—C(═NR)—S—R, halogen-C(═O)—S—R,    halogen-C(═S)—S—R, halogen-C(═NR)—S—R, halogen-S(═O)—S—R,    halogen-S(═O)₂—S—R, R—S—C(═O)—S—R, R—S—C(═S)—S—R, R—S—C(═NR)—S—R,    R—S—S(═O)—S—R, R—S—S(═O)₂—S—R, Y—C(═O)—S—R, Y—C(═S)—S—R,    Y—C(═NR)—S—R, Y—S(═O)—S—R, Y—S(═O)₂—S—R, (X⁶)(X⁷)P(═S)—S—R, (X⁶)(X⁷)    P(═O)—S—R, X⁸—C(═O)—S—R, R—C(═S)—S—R, R—C(═NR)—S—R,    (X⁹)₂N—C(═O)—S—R, (X⁹)₂N—C(═S)—S—R, R—NR—C(═NR)—S—R, X⁹—O—C(═S)—S—R,    R—S(═O)—S—R, R—S(═O)₂—S—R, R—NR—S(═O)₂—S—R, R—NR—S(═O)—S—R,    (R—NR—)₂P(═S)—S—R, (R—NR—)₂P(═O)—S—R, R—(R—O—)P(═O)—S—R,    R—(R—O—)P(═S)—S—R, R—(R—NR—)P(═O)—S—R, R—(R—NR—)P(═S)—S—R,    (R—O—)(R—NR—)P(═O)—S—R, (R—O—)(R—NR—)P(═S)—S—R, (R—O—)P(═O)(S—R)₂,    (R—O—)P(═S)(S—R)₂, (R—S—)P(═O)(S—R)₂, (R—NR—)P(═O)(S—R)₂,    (R—NR—)P(═S)(S—R)₂, R—P(═O)(S—R)₂, R—P(═S)(S—R)₂,    (R—O—)(Y)P(═O)—S—R, (R—O—)(Y)P(═S)—S—R, (R—NR—)(Y)P(═O)—S—R,    (R—NR—)(Y)P(═S)—S—R, R—(Y)P(═O)—S—R, R—(Y)P(═S)—S—R, P(═O)(S—R)₃,    P(═S)(S—R)₃, P(NR)(S—R)₃, Y—P(═O)(S—R)₂, Y—P(═S)(S—R)₂,    Y—P(NR)(S—R)₂, Y₂P(═O)—S—R, Y₂P(═S)—S—R or Y₂P(NR)—S—R, in which R,    Y, Z, X⁴, X⁵, X⁶, X⁷, X⁸, X⁹ and t have the above mentioned meanings    and s is 1 or 2.

Carboxylic acid chlorides, dicarboxylic acid chlorides, dicarboxylicacid dichlorides, halogen-containing phosphorus compounds, particularlypreferably P(═O)Cl₃ or P(═S)Cl₃, or halogen-containing organosiliconcompounds of the form X⁴X⁵X⁴SiCl, X⁴X⁵X⁴SiBr, X⁴X⁵SiCl₂, X⁴X⁵SiBr₂,X⁴SiCl₃ or X^(X)SiBr₃, particularly preferably Me₃SiCl, C₃H₇—SiCl₃,C₄H₉—SiCl₃, C₈H₁₇—SiCl₃ or C₁₆H₃₃—SiCl₃, can preferably be used asorganic or inorganic acid chlorides.

The reaction can be effected in the presence of an auxiliary base in asuitable solvent.

For example, amines, preferably dialkyl-substituted amines, particularlypreferably trialkyl-substituted amines, can be used as an auxiliarybase.

Solvents used may be aprotic solvents. Alkanes, preferably pentane,cyclohexane or heptane, aromatics or substituted aromatics, preferablybenzene, toluene, xylene or mesitylene, can be used as aprotic solvents.

Examples of organosilicon compounds of the formula (II) may be:

-   HS—CH₂—Si(—O—CH₂—CH₂—)₃N,-   HS—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   HS—CH₂—CH₂—CH₂—Si(—O—CH₂—CH₂—)₃N,-   HS—CH₂—CH(CH₃)—CH₂—Si(—O—CH₂—CH₂—)₃N,-   HS—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   HS—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N,-   HS—CH₂—CH₂—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N or-   HS—CH₂—CH(CH₃)—CH₂—Si(—O—CH(CH₃)—CH₂—)₃N.

The organosilicon compounds of the general formula (II) can be preparedby reacting compounds of the general formula (III),N((CX¹X³—CX¹X³—O)₃Si—G—S_(u)—G—Si(O—CX¹X²—CX¹X³)₃N  (III)in which u is ≦2, with alkali metals, alkaline earth metals or hydridecompounds thereof, with the aim of forming compounds of the generalformula alkali metal-S—G—Si(O—CX¹X²—CX¹X³)₃N orN(CX¹X³—CX¹X³—O)₃Si—G—S-alkaline earth metal-S—G—Si(O—CX¹X²—CX¹X³)₃N.

The invention furthermore relates to a process for the preparation ofthe organosilicon compounds according to the invention, which ischaracterized in that a compound of the general formula (IV),Q(—SH)  (IV)in which Q has the above mentioned meaning, is subjected to an additionreaction with an organosilicon compound containing at least one doublebond (═) and of the general formula (V)CX¹X²═CX²—G¹—Si(O—CX¹X²X—CX₁X³)₃N  (V)in which X¹, X² and X³ have the abovementioned meanings and—CX¹X²—CHX²—G¹ or HCX¹X²—CX²(−)—G¹ is G.

The addition reaction can be initiated by free radicals or catalysed.The addition reaction can be accelerated and/or controlled by UV light.

Preferred compounds of the general formula (IV) Q(—SH) may bethiocarboxylic acids of the general formula X⁸—C(═O)—SH. Preferredthiocarboxylic acids may be compounds X⁸—C(═O)—SH where X⁸ is(C₃-C₂₄)-alkyl, particularly preferably (C₇-C₂₄)-alkyl, veryparticularly preferably (C₁₁-C₁₇)-alkyl, aralkyl, preferably tolyl oraryl, preferably phenyl.

Preferred organosilicon compounds of the general formula (V) may beCH₂═CH—CH₂—Si(O—CX¹X²—CX¹X³)₃N, CH₂═CH—CH₂—CH₂—Si(O—CX¹X²—CX¹X³)₃N,CH(CH₃)═CH—CH₂—Si(O—CX¹X² —CX¹X³ )₃N or CH₂═CH—Si(O—CX¹X²—CX¹X³)₃N, veryparticularly preferably CH₂═CH—CH₂—Si(O—CH₂—CH₂)₃N,CH₂═CH—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, CH(CH₃)═CH—CH₂—Si(O—CH₂—CH₂)₃N orCH₂═CH—Si(O—CH₂—CH₂)₃N.

The invention furthermore relates to a process for the preparation ofthe organosilicon compounds according to the invention, which ischaracterized in that a compound of the general formula (VI)Q(—S—X¹⁰)  (VI)in which Q and X¹⁰ have the above mentioned meanings, is reacted with acompound of the general formula (VII),halogen-G—Si(O—CX¹X²—CX¹X³)₃N  (VII)in which G, X¹, X² and X³ have the above mentioned meanings.

Preferred halogen may be Cl, Br and I.

Preferably, compounds of the general formula (VI) may be Q—(S-alkalimetal) and compounds of the general formula (VII) may beCl—G—Si(O—CH₂—CH₂)₃N. Very particularly preferably, compounds of thegeneral formula (VI) X⁸—C(O)—S-alkali metal or R—C(S)—S-alkali metal canbe reacted with compounds of the general formula (VII)Cl—CH₂—Si(O—CH₂—CH₂)₃N,

-   Cl—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, Cl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N,-   Cl—CH₂—CH(CH₃)—CH₂—Si(O—CH₂—CH₂)₃N or-   Cl—CH(CH₃)—CH₂—CH₂—Si(O—CH₂—CH₂)₃N. The preparation of the compound    of the general formula (VI) Q(—S—X¹⁰) or the reaction thereof with    compounds of the general formula (VII) halogen-G—Si(O—CX¹X²—CX¹X³)₃N    can be carried out by means of phase-transfer catalysis.

The invention furthermore relates to a process for the preparation ofthe organosilicon compounds according to the invention, which ischaracterized in that at least one silane of the general formulaeVIII-XI,Q—[S—G—Si(alkoxy)₃]  (VIII)(alkoxy)₃Si—G—S—C(═O)—Z—C(═O)—S—G—Si(alkoxy)₃  (IX)(alkoxy)₃Si—G—S—C(═S)—Z—C(═S)—S—G—Si(alkoxy)₃  (X)(alkoxy)₃Si—G—S—C(═NR)—Z—C(═NR)—S—G—Si(alkoxy)₃  (XI)in which G, Q, and z have the above mentioned meanings and alkoxy,independently of one another, are (C₁-C₂₄)-alkoxy, preferably methoxy,ethoxy or propoxy, is reacted with compounds of the general formula XII,(HO—CX¹X²—CX¹X³—)₃N  (XII)in which X¹, X², and X³ have the abovementioned meanings, withelimination of (alkoxy)-H, and (alkoxy)-H is separated from the reactionmixture. The reaction can be effected with or without catalysis. The(alkoxy)-H can be separated continuously or batchwise from the reactionmixture.

Examples of compounds of the general formula XII include:triethanolamine, triisopropanolamine and [HO—CH(phenyl)CH₂]₃N.

A low water content of the compounds of the formula XII which are usedmay have an advantageous effect on the composition and the productproperties of the compounds according to the invention. Preferably, thecompounds of the formula XII can have a water content of less than 1% byweight, particularly preferably of less than 0.5% by weight, veryparticularly preferably of less than 0.3% by weight, exceptionallypreferably of less than 0.2% by weight.

The reaction can be carried out in typical organic solvents having aboiling point of less than 200° C., preferably less than 160° C,particularly preferably less than 130° C., very particularly preferablyless than 100° C.

A reaction in the absence of organic solvents may be preferred.

One of the starting compounds may be present as a melt, suspension orsolution.

One or more of the reaction products may be present as a melt,suspension or solution.

The reaction in the absence of organic solvents may be preferred owingto the higher yields achieved compared with the reactions in solvents.

The reaction in the absence of organic solvents may be preferred owingto the higher purity achieved for the products obtained compared withthe reactions in solvents.

The reaction in the absence of organic solvents may be preferred owingto the absence of traces of solvent in the products obtained.

The reaction in the absence of organic solvents may be preferred owingto the minimization of volatile organic compounds (VOC) in the productsobtained.

The reaction in the absence of organic solvents may be preferred owingto the omission of a drying step in the process, for removing traces ofsolvent, compared with the reaction in organic solvents.

In the process according to the invention, metal-free ormetal-containing catalysts can be used as a catalyst. Metal compounds ofthe 3rd-7th group, of the 13th-14th group and/or of the lanthanide groupmay be used as metal-containing catalysts.

Transition metal compounds may be used as metal-containing catalysts.

The metal-containing catalysts may be metal compounds, such as, forexample, metal chlorides, metal oxides, metal oxychlorides, metalsulphides, metal sulphochlorides, metal alcoholates, metal thiolates,metal oxyalcoholates, metal amides, metal imides or transition metalcompounds having multiple bound ligands.

For example metal compounds used may be halides, amides or alcoholatesof the 3rd main group (M³⁺=B,Al,Ga,In,Tl: M³⁺(OMe)₃, M³⁺(OEt)₃,M³⁺(OC₃H₇)₃, M³⁺(OC₄H₉)₃),

-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the lanthanide group (rare earth metals,    atomic numbers 58 to 71 in the Periodic Table of the Elements),-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the 3rd subgroup (M³⁺=Sc,Y,La: M³⁺(OMe)₃,    M³⁺(OEt)₃, M³⁺(OC₃H₇)₃, M³⁺(OC₄H₉)₃, cpM³⁺(Cl)₂, cp cpM³⁺(OMe)₂,    cpM³⁺(OEt)₂, cpM³⁺(NMe₂)₂ where cp=cyclopentadienyl),-   halides, sulphides, amides, thiolates or alcoholates of the 4th main    group (M⁴⁺=Si,Ge,Sn,Pb: M⁴⁺(OMe)₄, M⁴⁺(OEt)₄, M⁴⁺(OC₃H₇)₄,    M⁴⁺(OC₄H₉)₄; M²⁺=Sn,Pb: M²⁺(OMe)₂, M²⁺(OEt)₂, M²⁺(OC₃H₇)₂, M²    ⁺(OC₄H₉)₂), tin dilaurate, tin diacetate, Sn(OBu)₂,-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the 4th subgroup (M⁴⁺=Ti,Zr,Hf: M⁴⁺(F)₄,    M⁴⁺(Cl)₄, M⁴⁺(Br)₄, M⁴⁺(I)₄, M⁴⁺(OMe)₄, M⁴⁺(OEt)₄, M⁴⁺(OC₃H₇)₄,    M⁴⁺(OC₄H₉)₄, cp₂Ti(Cl)₂, cp₂Zr(Cl)₂, cp₂Hf(Cl)₂, cp₂Ti(OMe)₂,    cp₂Zr(OMe)₂, cp₂Hf(OMe)₂, cpTi(Cl)₃, cpZr(Cl)₃, cpHf(Cl)₃,    cpTi(OMe)₃, cpZr(OMe)₃, cpHf(OMe)₃, M⁴⁺(NMe₂)₄, M⁴⁺(NEt₂)₄,    M⁴⁺(NHC₄H₉)₄),-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the 5th subgroup (M⁵⁺, M⁴⁺ or M³⁺=V,Nb,Ta:    M⁵⁺(OMe)₅, M⁵⁺(OEt)₅, M⁵⁺(OC₃H₇)₅, M⁵⁺(OC₄H₉)₅, M³⁺O(OMe)₃,    M³⁺O(OEt)₃, M³⁺O(OC₃H₇)₃, M³⁺O(OC₄H₉)₃, cpV(OMe)₄, cpNb(OMe)₃,    cpTa(OMe)₃, cpV(OMe)₂, cpNb(OMe)₃, cpTa(OMe)₃),-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the 6th subgroup (M⁶⁺, M⁵⁺ or M⁴⁺=Cr,Mo,W:    M⁶⁺(OMe)₆, M⁶⁺(OEt)₆, M⁶⁺(OC₃H₇)₆, M⁶⁺(OC₄H₉)₆, M⁶⁺O(OMe)₄,    M⁶⁺O(OEt)₄, M⁶⁺O(OC₃H₇)₄, M⁶⁺O(OC₄H₉)₄, M⁶⁺O₂(OMe)₂, M⁶⁺O₂(OEt)₂,    M⁶⁺O₂(OC₃H₇)₂, M⁶⁺O₂(OC₄H₉)₂, M⁶⁺O₂(OSiMe₃)₂) or-   halides, oxides, sulphides, imides, alcoholates, amides, thiolates    and combinations of said substituent classes with multiple bound    ligands to compounds of the 7th subgroup (M⁷⁺, M⁶⁺, M⁵⁺ or    M⁴⁺=Mn,Re: M⁷⁺O(OMe)₅, M⁷⁺O(OEt)₅, M⁷⁺O(OC₃H₇)₅, M⁷⁺O(OC₄H₉)₅,    M⁷⁺O₂(OMe)₃, M⁷⁺O₂(OEt)₃, M⁷⁺O₂(OC₃H₇)₃, M⁷⁺O₂(OC₄H₉)₃,    M⁷⁺O₂(OSiMe₃)₃, M⁷⁺O₃(OSiMe₃), M⁷⁺O₃(CH₃)).

The metal and transition metal compounds may have a free coordinationsite on the metal.

Metal or transition metal compounds which are formed by addition ofwater to hydrolysable metal or transition metal compounds can also beused as catalysts.

For example, titanium alkoxides can be used as metal-containingcatalysts.

In a particular embodiment titanates, such as, for example,tetra-n-butyl orthotitanate, tetraethyl orthotitanate, tetra-n-propylorthotitanate or tetraisopropyl orthotitanate, can be used as catalysts.

Organic acids can be used as metal-free catalysts.

For example, trifluoroacetic acid, trifluoromethanesulphonic acid,p-toluenesulphonic acid, trialkylammonium compounds R₃NH⁺X⁻ or bases,such as, for example, trialkylamines NR₃ can be used as organic acids.

The process according to the invention can be carried out at atmosphericpressure or reduced pressure, preferably between 1 and 600 mbar,particularly preferably between 5 and 400 mbar, very particularlypreferably between 5 and 200 mbar.

The process according to the invention can be carried out in thetemperature range between 50° C. and 200° C., preferably between 70° C.and 180° C., particularly preferably between 90° C. and 150° C.

Substances which promote the transport of water through the product byformation of azeotropic mixtures can be added to the reaction mixturebefore or during the reaction. The corresponding substances may becyclic or straight-chain aliphatics, aromatics, mixed aromatic-aliphaticcompounds, ethers, alcohols or acids. For example, hexane, cyclohexane,benzene, toluene, ethanol, propanol, isopropanol, butanol, ethyleneglycol, tetrahydrofuran, dioxane, formic acid, acetic acid, ethylacetate or dimethylformamide may be used.

The reaction can be carried out continuously or batchwise.

In the process according to the invention, additives can be added to thereaction mixture before, during or after the reaction. The additives canpreferably be added before the reaction. The additives may reduceelectrophilic or nucleophilic cleavage of the Q—S bond in formula I.

For avoiding condensation reactions, it may be advantageous to carry outthe reaction in an anhydrous environment, ideally in an inert gasatmosphere.

The organosilicon compounds according to the invention can be used asadhesion promoters between inorganic materials (for example glassfibres, metals, oxidic fillers, silicas) and organic polymers (forexample thermosetting plastics, thermoplastics, elastomers) or ascrosslinking agents and surface-modifying agents. The organosiliconcompounds according to the invention can be used as coupling reagents infilled rubber mixtures, for example tyre treads.

The invention furthermore relates to rubber mixtures which arecharacterized in that they contain rubber, filler, such as, for example,precipitated silica, optionally further rubber auxiliaries, and at leastone of the organosilicon compounds according to the invention and of thegeneral formula (I).

The organosilicon compounds according to the invention and of thegeneral formula (I) can be used in amounts of from 0.1 to 50% by weight,preferably from 0.1 to 25% by weight, particularly preferably from 1 to20% by weight, based on the amount of the rubber used.

The addition of the organosilicon compounds according to the inventionand of the general formula (I) and the addition of the fillers can beeffected at material temperatures of from 100 to 200° C. However, theycan also be effected at lower temperatures of from 40 to 100° C., forexample together with further rubber auxiliaries.

The organosilicon compounds according to the invention can be added tothe mixing process both in pure form and after application to an inertorganic or inorganic support, and after a preliminary reaction with anorganic or inorganic support. Preferred support materials may beprecipitated or pyrogenic silicas, waxes, thermoplastics, natural orsynthetic silicates, natural or synthetic oxides, preferably alumina, orcarbon blacks. Furthermore, the organosilicon compounds according to theinvention can also be added to the mixing process after preliminaryreaction with the filler to be used.

The organosilicon compounds according to the invention can be added tothe mixing process after being physically mixed with an organicsubstance or with a mixture of organic substances. The organic substanceor the mixture of organic substances may contain polymers or oligomers.The polymers or oligomers may be heteroatom-containing polymers oroligomers, for example ethylene-vinyl alcohol, ethylene-vinyl acetate,polyvinyl acetate and/or polyvinyl alcohols. Polymers or oligomers maybe saturated or unsaturated elastomers, preferably emulsion SBR and/orsolution SBR. The melting point of the mixture of organosiliconcompounds according to the invention and organic substance or a mixtureof organic substances may be between 50 and 200° C., preferably between70 and 180° C., particularly preferably between 70 and 150° C., veryparticularly preferably between 70 and 130° C., exceptionally preferablybetween 90 and 110° C. The organic substance or the mixture of organicsubstances may contain at least one olefinic wax and/or long-chaincarboxylic acids.

Fillers which may be used for the rubber mixtures according to theinvention are the following fillers:

-   -   Carbon blacks: the carbon blacks to be used can be prepared by        the flame black, furnace, gas black or thermal black process.        The carbon blacks may have a BET surface area of from 20 to 200        m²/g. The carbon blacks can optionally also be doped, such as,        for example, with Si.    -   Amorphous silicas, prepared, for example, by precipitation of        solutions of silicates (precipitated silicas) or flame        hydrolysis of silicon halides (pyrogenic silicas). The amorphous        silicas may have a specific surface area of from 5 to 1000 m²/g,        preferably from 20 to 400 m²/g (BET surface area) and a primary        particle size of from 10 to 400 nm. The silicas can optionally        also be present as mixed oxides with other metal oxides, such as        Al, Mg, Ca, Ba, Zn and titanium oxides.    -   Synthetic silicates, such as aluminium silicate or alkaline        earth metal silicates, for example magnesium silicate or calcium        silicate. The synthetic silicates may have BET surface areas of        from 20 to 400 m²/g and primary particle diameters of from 10 to        400 nm.    -   Synthetic or natural aluminas and aluminium hydroxides.    -   Natural silicates, such as kaolin and other naturally occurring        silicas.    -   Glass fibres and glass fibre products (mats, extrudates) or        glass microspheres.

Amorphous silicas, prepared by precipitation of solutions of silicates(precipitated silicas), having BET surface areas of from 20 to 400 m²/gin amounts of from 5 to 150 parts by weight, based in each case on 100parts of rubber, can preferably be used.

Said fillers can be used alone or as a mixture. In a particularlypreferred embodiment of the process, from 10 to 150 parts by weight oflight fillers, optionally together with from 0 to 100 parts by weight ofcarbon black, and from 1 to 20 parts by weight of a compound of theorganosilicon compounds according to the invention, based in each caseon 100 parts by weight of rubber, can be used for the preparation of themixtures.

In addition to natural rubber, synthetic rubbers are also suitable forthe preparation of the rubber mixtures according to the invention.Preferred synthetic rubbers are described, for example, in W. Hofmann,Kautschuktechnologie [Rubber technology], Genter Verlag, Stuttgart 1980.They comprise, inter alia,

-   -   polybutadiene (BR),    -   polyisoprene (IR),    -   styrene/butadiene copolymers, for example emulsion SBR (E-SBR)        or solution SBR (S-SBR), preferably having a styrene content of        from 1 to 60% by weight, particularly preferably from 2 to 50%        by weight, based on the total polymer,    -   chloroprene (CR),    -   isobutylene/isoprene copolymers (IIR),    -   butadiene/acrylonitrile copolymers, preferably having an        acrylonitrile content of from 5 to 60% by weight, preferably        from 10 to 50% by weight, based on the total polymer (NBR),    -   partly hydrogenated or completely hydrogenated NBR rubber        (HNBR),    -   ethylene/propylene/diene copolymers (EPDM) or    -   above mentioned rubbers which additionally have functional        groups, such as, for example, carboxyl, silanol or epoxy groups,        for example epoxidized NR, carboxy-functionalized NBR or        silanol-(—SiOH) or silyloxy-functionalized (—Si—OR) SBR,        and blends of these rubbers. For the preparation of car tyre        treads, anionically polymerized S-SBR rubbers (solution SBR)        having a glass transition temperature above −50° C. and blends        thereof with diene rubbers are of particular interest.

The rubber vulcanizates according to the invention may contain furtherrubber auxiliaries, such as reaction accelerators, antiageing agents,heat stabilizers, light stabilizers, antiozonants, processingauxiliaries, plasticizers, tackifiers, blowing agents, dyes, pigments,waxes, extenders, organic acids, retardants, metal oxides andactivators, such as diphenylguanidine, triethanolamine, polyethyleneglycol, alkoxy-terminated polyethylene glycol alkyl-O—(CH₂—CH₂—O)_(yI)—Hwhere y^(I)=2-25, preferably y^(I)=2-15, particularly preferablyy^(I)=3-10, very particularly preferably y^(I)=3-6, or hexanetriol,which are known to the rubber industry.

The vulcanization of the rubber mixtures according to the invention canbe carried out without addition of nitrogen-containing activators, suchas, for example, guanidines and amines. In a preferred embodiment, therubber vulcanizate may be free of guanidine derivatives.

The rubber auxiliaries can be used in known amounts which depend, interalia, on the intended use. Customary amounts may be, for example,amounts of from 0.1 to 50% by weight, based on rubber. Sulphur orsulphur-donating substances may be used as crosslinking agents. Over andabove this, the rubber mixtures according to the invention may containvulcanization accelerators. Examples of suitable vulcanizationaccelerators may be mercaptobenzothiazoles, sulphenamides, guanidines,thiurams, dithiocarbamates, thioureas and thiocarbonates. Thevulcanization accelerators and sulphur can be used in amounts of from0.1 to 10% by weight, preferably from 0.1 to 5% by weight, based onrubber.

The vulcanization of the rubber mixtures according to the invention canbe effected at temperatures of from 100 to 200° C., preferably from 130to 180° C., optionally under pressure of from 10 to 200 bar. The mixingof the rubbers with the filler, optionally rubber auxiliaries and theorganosilicon compound according to the invention can be carried out inknown mixing units, such as roll mills, internal mixers and mixingextruders.

The rubber mixtures according to the invention can be used for theproduction of mouldings, for example for the production of pneumatictyres, tyre treads, cable sheaths, hoses, drive belts, conveyor belts,roll coverings, tyres, shoe soles, sealing rings and damping elements.

The organosilicon compounds according to the invention have theadvantage that no readily volatile alcohol, usually methanol or ethanol,is liberated during the hydrolysis of the Si—O—R bonds and at the sametime the reactivity with the inorganic filler and the organic polymer isstill high. The processing properties of the raw mixtures and thedynamic properties of the vulcanizates give a very good, balanced set ofvalues overall.

EXAMPLES

The HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N used is synthesized fromHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₃)₃ with triethanolamine in the presence ofTi(OBu)₄ at temperatures of 110-130° C. under reduced pressure and in areaction time of 180-360 min by transesterification in the absence of asolvent.

The HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N contains between 1 and 6% by weightof Cl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, depending on the quality of theHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₃)₃ used.

Cl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₃)₃ is present as a secondary constituent inthe HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₃)₃ used and is converted intoCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N under the reaction conditions.

Comparative Example 1

Preparation of CH₃—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

38.5 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 10 min at 0° C. 29.4 g of acetyl chloride are added dropwiseto the mixture at a temperature between −5° C. and 0° C. After stirringfor 60 min at between 0° and room temperature, the suspension formed isheated to 80° C. for 3 h. Thereafter, the suspension is filtered, thefiltercake is washed with toluene, the filtrates obtained are combinedand the solvent is removed on a rotary evaporator. 114 g of viscousproduct are obtained. According to NMR analyses, the product contains 87mol % of CH₃—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 9 mol % ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 3 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 1

Preparation of C₇H₁₅—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

40.6 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 10 min at 0° C. 65.3 g of octanoyl chloride are addeddropwise to the mixture at a temperature between −5° C. and 0° C. Afterstirring for 60 min at between 0° and room temperature, the suspensionobtained is filtered, the filtercake is washed, the filtrates obtainedare combined and the solvent is removed on a rotary evaporator. 141.6 gof viscous product are obtained. According to NMR analyses, the productcontains 93 mol % of C₇H₁₅—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 5 mol %of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 2 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 2

Preparation of C₁₁H₂₃—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

38.5 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 10 min at 0° C. 83.2 g of dodecanoyl chloride are addeddropwise to the mixture at a temperature between −5° C. and 0° C. Afterstirring for 15 h at between 0° and room temperature, the suspensionobtained is filtered, the filtercake is washed, the filtrates obtainedare combined and the solvent is removed on a rotary evaporator. 162.4 gof viscous product are obtained. According to NMR analyses, the productcontains >86 mol % of C₁₁H₂₃—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 9 mol %of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 3 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 3

Preparation of C₁₅H₃₁—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

38.5 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 15 min at 0° C. 104.5 g of palmitoyl chloride are addeddropwise to the mixture at a temperature between −10° C. and 0° C. Afterstirring for 18 h at room temperature the suspension obtained isfiltered, the filtercake is washed, the filtrates obtained are combinedand the solvent is removed on a rotary evaporator. 186.3 g of viscousproduct are obtained. According to NMR analyses, the product contains 88mol % of C₁₅H₃₁—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 8 mol % ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 3 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 4

Preparation ofN(CH₂CH₂—O)₃Si(CH₂)₃S—C(O)—C₄H₈—C(O)—S(CH₂)₃Si(O—CH₂CH₂)₃N

40.5 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 15 min at 0° C. 53.5 g of adipoyl dichloride are addeddropwise to the mixture at a temperature between −10° C. and 0° C. Afterstirring for 2 h at room temperature, the suspension formed is heated to70° C. for 2 h. The suspension obtained is filtered, the filtercake iswashed, the filtrates obtained are combined and the solvent is removedon a rotary evaporator. 98.4 g of viscous product are obtained.According to NMR analyses, the product contains 93 mol % ofN(CH₂CH₂—O)₃Si(CH₂)₃S—C(O)—C₄H₈—C(O)—S(CH₂)₃Si(O—CH₂CH₂)₃N, 2 mol % ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 4 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 5

Preparation ofN(CH₂CH₂—O)₃Si(CH₂)₃S—C(O)—C₁₀H₂₀—C(O)—S(CH₂)₃Si(O—CH₂CH₂)₃N

38.5 g of triethylamine are added at 0° C. to a solution of 100 g ofHS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene. The mixture isstirred for 15 min at 0° C. 50.8 g of dodecanedioyl chloride are addeddropwise to the mixture at a temperature between −10° C. and 0° C. Afterstirring for 2 h at room temperature, the suspension formed is heated to70° C. for 3 h. The suspension obtained is cooled and filtered, thefiltercake is washed with toluene, the filtrates obtained are combinedand the solvent is removed on a rotary evaporator. 132.4 g of viscousproduct are obtained. According to NMR analyses, the product contains 91mol % of N(CH₂CH₂—O)₃Si(CH₂)₃S—C(O)—C₁₁H₂₀—C(O)—S(CH₂)₃Si(O—CH₂CH₂)₃N, 2mol % of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 4 mol % ofCl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, based on the silicon-containingconstituents.

Example 6

Rubber Investigations

The formulation used for the rubber mixtures is stated in Table 1 below.There, the unit phr denotes parts by weight based on 100 parts of theraw rubber used. The organosilicon compounds according to the inventionare used in equimolar amounts, i.e. in an amount of substance identicalto the amount of the silane of Comparative Example 1. The followingcoupling agents are investigated:

-   Mixture 1: Comparative Example 1-   Mixture 2: 3-octanoylthio-1-propyltriethoxysilane, Trade name: NXT    from General Electric-   Mixture 3: Example 1-   Mixture 4: Example 2-   Mixture 5: Example 3

The general process for the preparation of rubber mixtures and thevulcanizates thereof is described in the book: “Rubber TechnologyHandbook”, W. Hofmann, Hanser Verlag 1994. TABLE 1 Mixture 1 MixtureMixture Mixture Comparative 2 3 4 Mixture 5 Substance Ex. 1 NXT Ex. 1Ex. 2 Ex. 3 (Coupling agent) [phr] [phr] [phr] [phr] [phr] 1st stageBuna VSL 5025-1 96 96 96 96 96 Buna CB 24 30 30 30 30 30 Ultrasil 7000GR 80 80 80 80 80 Coupling agent 7 8.8 9 10.4 11.7 ZnO 3 3 3 3 3 Stearicacid 2 2 2 2 2 Naftolen ZD 10 10 10 10 10 Vulkanox 4020 1.5 1.5 1.5 1.51.5 Protektor G 3108 1 1 1 1 1 2nd stage Batch stage 1 3rd stage Batchstage 2 Vulkacit CZ 1.5 1.5 1.5 1.5 1.5 Perkacit TBzTD 0.2 0.2 0.2 0.20.2 Sulphur 2.1 2.1 2.1 2.1 2.1

The polymer VSL 5025-1 is a solution-polymerized SBR copolymer fromBayer AG, having a styrene content of 25% by weight and a butadienecontent of 75% by weight. The copolymer contains 37.5 phr of oil and hasa Mooney viscosity (ML 1+4/100° C.) of 50.

The polymer Buna CB 24 is a cis-1,4-polybutadiene (neodymium grade) fromBayer AG, having a cis-1,4 content of at least 96% and a Mooneyviscosity of 44±5.

Ultrasil 7000 GR is a readily dispersible silica from Degussa AG and hasa BET surface area of 170 m²/g.

Naftolen ZD from Chemetall is used as an aromatic oil, Vulkanox 4020 isPPD from Bayer AG and Protektor G3108 is an antiozonant wax fromParamelt B.V. Vulkacit CZ (CBS) is a commercial product from Bayer AG.Perkacit TBzTD (tetrabenzylthiuram tetrasulphide) is a product fromFlexsys N.V.

The rubber mixtures are prepared in an internal mixer according to themixing method in Table 2. TABLE 2 Stage 1 Settings Mixing unit Werner &Pfleiderer E-Typ Speed 90 min⁻¹ Ram pressure 5.5 bar Empty volume 1.58 lDegree of filling 0.56 Flow-through temp. 70° C. Mixing process 0 to 1min Buna VSL 5025-1 + Buna CB 24 1 to 2 min ½ silica, ZnO, stearic acid,Naftolen ZD, coupling agent 2 to 4 min ½ silica, Vulkanox, Protektor 4to 5 min Mixing 5 min Aeration 5 to 6 min Mixing and discharge Batchtemp. 140-150° C. Storage 24 h at room temperature Stage 2 SettingsMixing unit As in stage 1 except for: Speed 80 min⁻¹ Flow-through temp.80° C. Degree of filling 0.54 Mixing process 0 to 2 min Break up stage 1batch 2 to 5 min Maintain batch temperature at 145° C. by speedvariation 5 min Discharge Batch temp. 140-150° C. Storage 4 h at roomtemperature Stage 3 Settings Mixing unit As in stage 1 except for Speed40 min⁻¹ Degree of filling 0.52 Flow-through temp. 50° C. Mixing process0 to 2 min Stage 2 batch, accelerator, sulphur 2 min Discharge and formhide on laboratory mixing mill (diameter 200 mm, length 450 mm,flow-through temperature 50° C.) Homogenization: cut up 5 times left, 5times right and 3 times with wide roll nip (6 mm) and 3 times withnarrow roll nip (3 mm) withdraw hide. Batch temp. <110° C.

The methods for rubber testing are listed in Table 3. TABLE 3 Physicaltesting Standard/Conditions ML 1 + 4, 100° C., 3rd stage DIN 53523/3,ISO 667 Ball Rebound, 60° C. (%) ASTM D 5308 Goodrich flexometer test,DIN 53533, ASTM D 623 A 0.250 inch stroke, 25 min, 23° C. Contacttemperature (° C.) Insertion temperature (° C.) Permanent set (%)

Table 4 shows the results of the rubber test. The mixtures arevulcanized to t99% of the rheometer test but for not longer than 30 minat 165° C. TABLE 4 Mixture Mixture Mixture Mixture Mixture Unit 1 2 3 45 Raw mixture data ML 1 + 4, [—] 64 59 57 56 54 3rd stage Vulcanizatedata Ball rebound, [%] 66.7 67.0 69.8 69.3 69.0 60° C. Contact [° C.] 5758 50 50 53 temperature Insertion [° C.] 109 111 96 98 102 temperaturePermanent set [%] 2.0 2.5 1.7 1.7 1.8

The results of Table 4 show that the viscosity of the mixture can bereduced by lengthening the blocking group from acetyl through octanoylto palmityl. Comparison of the mixture 2 with the mixture 3 shows thatthe viscosity too is reduced by the modification of the silane. Thus,the silanes according to the invention are distinguished by betterprocessability compared with the prior art.

On consideration of the vulcanizate results, it is evident that both theball rebound and the heat build-up of the mixtures 3, 4 and 5 comprisingthe silanes according to the invention are substantially improvedcompared with the mixtures 1 and 2.

Thus, it is found that advantages both in the processability and in thedynamic behaviour can be produced exclusively by the combination of themodification of the silica-active coupling group and simultaneousblocking of the sulphur group.

Both the higher ball rebound and the lower heat build-up indicate thattyre treads comprising the silanes according to the invention lead to alower rolling resistance and hence fuel consumption. In addition, thedynamic heat build-up is lower, which increases the longevity of thetyre. By means of the organosilicon compounds according to theinvention, the processability of the rubber mixture and at the same timethe dynamic behaviour can therefore be improved.

In addition, the organosilicon compounds according to the invention aredistinguished in that no volatile alcohol is liberated during themixing.

Example 7

Preparation of C₄H₉—NH—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

70 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 44.5 g of O═C═N—C₄H₉ (fromSigma-Aldrich) are combined in 100 g of toluene (Seccosolv) under inertgas at 25° C. in a flask and are stirred for 24 h. Stirring is theneffected for 5 h at 60° C. The solution obtained is freed from volatileconstituents on a rotary evaporator at 80° C. in vacuo. 100 g of aviscous dark, orange oil are obtained.

Example 8

Preparation of C₈H₁₇—NH—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

40 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 25 g of O═C═N—C₈H₁₇ (fromSigma-Aldrich) are combined in 100 g of toluene (Seccosolv) under inertgas at 25° C. in a flask and are stirred for 24 h. Stirring is theneffected for 5 h at 60° C. The solution obtained is freed from volatileconstituents on a rotary evaporator at 80° C. in vacuo. 65 g of aviscous yellow oil are obtained.

Example 9

Preparation of C₆H₅—NH—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

75 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 55 g of O═C═N—C₆H₅ (from VWR)are combined in 100 g of toluene (Seccosolv) under inert gas at 25° C.in a flask and are stirred for 48 h. A colourless precipitate forms. Thesuspension obtained is filtered and the filtercake is washed with 500 mlof pentane. The filtercake is then dried at 80-90° C. in vacuo. 110 g ofa colourless solid are obtained.

Example 10

Preparation of C₄H₉—NH—C(S)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

70 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 50 g of S═C═N—C₄H₉ (fromKMF-Laborchemie) are combined in 100 g of toluene (Seccosolv) underinert gas at 25° C. in a flask and are stirred for 48 h. Stirring isthen effected for 5 h at 60° C. The solution obtained is freed fromvolatile constituents on a rotary evaporator at 80° C. in vacuo. 102 gof a viscous orange-brown oil are obtained.

Example 11

Preparation of C₈H₁₇—NH—C(S)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

30 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 25 g of S═C═N—C₈H₁₇ (fromKMF-Laborchemie) are combined in 100 g of toluene (Seccosolv) underinert gas at 25° C. in a flask and are stirred for 24 h. Stirring isthen effected for 5 h at 60° C. The solution obtained is freed fromvolatile constituents on a rotary evaporator at 80° C. in vacuo. 55 g ofa viscous yellow-orange oil are obtained.

Example 12

Preparation of C₆H₅—NH—C(S)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

75 g of HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N and 50 g of S═C═N—C₆H₅ (from VWR)are combined in 100 g of toluene (Seccosolv) under inert gas at 25° C.in a flask and are stirred for 48 h. A wax-coloured precipitate, whichdoes not dissolve even in an additional 235 g of toluene, forms.Stirring is then effected for 5 h at 60° C. The suspension obtained isfiltered and the filtercake is washed with 700 ml of pentane. Thefiltercake is then dried at 80-90° C. in vacuo. 100 g of a colourlesssolid are obtained.

Example 13

Preparation of Me₃Si—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

44.5 g of triethylamine are added at 1° C. to a cooled solution of 100 gof HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene (Seccosolv). Themixture is stirred for 10 min at 3-6° C. 47.8 g of trimethylsilylchloride are added dropwise to the mixture at a temperature between 1°C. and 10° C. After stirring for 60 min, the suspension formed is heatedto 70° C. for 5 h, then cooled and then filtered. The filtercake iswashed, the filtrates obtained are combined and the solvent is removedon a rotary evaporator. 129 g of orange viscous product are obtained.

Example 14

Preparation of C₁₆H₃₃—Si—[S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N]₃

44.5 g of triethylamine are added at 0° C. to a cooled solution of 100 gof HS—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N in 1000 ml of toluene (Seccosolv). Themixture is stirred for 10 min at 2-4° C. 46.8 g of C₁₆H₃₃—SiCl₃ areadded dropwise to the mixture at a temperature between 2° C. and 10° C.After stirring for 60 min, the suspension formed is heated to 70° C. for5 h, then cooled and then filtered. The filtercake is washed, thefiltrates obtained are combined and the solvent is removed on a rotaryevaporator. 130 g of orange viscous product are obtained.

Example 15

Preparation of C₆H₅—(C═O)—S—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N

36 g of triethylamine are added at 2° C. to a cooled solution of 100 gof HS—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N in 1000 ml of toluene (Seccosolv).The mixture is stirred for 10 min at 2-4° C. 49.2 g of benzoyl chlorideare added dropwise to the mixture at a temperature between 2° C. and 10°C. After stirring for 60 min, the suspension formed is heated to 65° C.for 5 h, then cooled and then filtered. The filtercake is washed, thefiltrates obtained are combined and the solvent is removed on a rotaryevaporator. 138 g of orange viscous product are obtained.

Example 16

Preparation of C₇H₁₅—(C═O)—S—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N

35.4 g of triethylamine are added at 3° C. to a cooled solution of 100 gof HS—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N in 1000 ml of toluene (Seccosolv).The mixture is stirred for 10 min at 2-4° C. 56.9 g of octanoyl chlorideare added dropwise to the mixture at a temperature between 20° C. and100° C. After stirring for 60 min, the suspension formed is heated to65-700° C. for 5 h, then cooled and then filtered. The filtercake iswashed, the filtrates obtained are combined and the solvent is removedon a rotary evaporator. 150 g of orange viscous product are obtained.

Example 17

Preparation of C₁₁H₂₃—(C═O)—S—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N

35.4 g of triethylamine are added at 3° C. to a cooled solution of 100 gof HS—CH₂—CH₂—CH₂—Si(O—CH(CH₃)—CH₂)₃N in 1000 ml of toluene (Seccosolv).The mixture is stirred for 10 min at 2-4° C. 76.6 g of dodecanoylchloride are added dropwise to the mixture at a temperature between 2°C. and 10° C. After stirring for 60 min, the suspension formed is heatedto 68-72° C. for 5 h, then cooled and then filtered. The filtercake iswashed, the filtrates obtained are combined and the solvent is removedon a rotary evaporator. 163 g of orange viscous product are obtained.

Example 18

Rubber Investigations

The formulation used for the rubber mixtures is stated in Table 5 below.There, the unit phr denotes parts by weight based on 100 parts of theraw rubber used. The organosilicon compounds according to the inventionare used in equimolar amounts, i.e. in an amount of substance identicalto the amount of the silane of Comparative Example 1.

The rubber mixtures are prepared in an internal mixer according to themixing method in Table 6. Table 3 lists the methods for rubber testing.TABLE 5 Mixture 6 Mixture 7 Mixture 8 Mixture 9 Comparative ExampleExample Example Substance Example 1 11 16 17 (coupling agent) [phr][phr] [phr] [phr] 1st stage Buna VSL 5025-1 96 96 96 96 Buna CB 24 30 3030 30 Ultrasil 7000 GR 80 80 80 80 Coupling agent 7.0 10.2 10.1 11.4 ZnO3 3 3 3 Stearic acid 2 2 2 2 Naftolen ZD 10 10 10 10 Vulkanox 4020 1.51.5 1.5 1.5 Protektor G 3108 1 1 1 1 2nd stage Batch stage 1 3rd stageBatch stage 2 Vulkacit CZ 1.5 1.5 1.5 1.5 Perkacit TBzTD 0.2 0.2 0.2 0.2Sulphur 2.1 2.1 2.1 2.1

TABLE 6 Stage 1 Settings Mixing unit Brabender 350 S mixing chamberSpeed 80 min⁻¹ Ram pressure 5 bar Empty volume 0.39 L Degree of filling0.68 Flow-through temp. 80° C. Mixing process 0 to 1 min Buna VSL5025-1 + Buna CB 24 1 to 2 min ½ silica, ZnO, stearic acid, Naftolen ZD,coupling agent 2 to 4 min ½ silica, Vulkanox, Protektor 4 to 5 minMixing 5 min Aeration 5 to 6 min Mixing and discharge Batch temperature140-150° C. Storage 24 h at room temperature Stage 2 Settings Mixingunit As in stage 1 except for: Speed 90 min⁻¹ Flow-through temp. 90° C.Degree of filling 0.66 Mixing process 0 to 2 min Break up stage 1 batch2 to 5 min Maintain batch temperature at 145° C. by speed variation 5min Discharge Batch temp. 140-150° C. Storage 4 h at room temperatureStage 3 Settings Mixing unit as in stage 1 except for: Speed 40 min⁻¹Degree of filling 0.64 Flow-through temp. 50° C. Mixing process 0 to 2min stage 2 batch, accelerator, sulphur 2 min discharge and form hide onlaboratory mixing mill (diameter 200 mm, length 450 mm, flow-throughtemperature 50° C.) Homogenization: cut up 5 times left, 5 times rightand 3 times with wide roll nip (6 mm) and 3 times with narrow roll nip(3 mm) withdraw hide. Batch temp. <110° C.

The results of the rubber investigations are summarized in Table 7.TABLE 7 Unit Mixture 6 Mixture 7 Mixture 8 Mixture 9 Raw mixture data ML1 + 4, [—] 130 96 69 65 3rd stage Vulcanizate data Puncture [° C.] 129117 124 122 temperature Permanent set [%] 3.6 2.9 2.8 2.8

As is evident from the results, mixtures 7 to 9 comprising theorganosilicon compounds according to the invention have a lowerviscosity and hence better processing properties. At the same time, theyalso have a smaller heat build-up and permanent set and henceadvantageous dynamic properties.

Example 19

Preparation of C₇H₁₅—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

100 g of S-[3-(triethoxysilyl)propyl] octanethioate [CAS No.220727-26-4], 41 g of triethanolamine (from BASF AG) and 1 g of NaOH arecombined under inert gas at 25° C. in an appartus and are heated to 130°C. Thereafter, stirring is effected for 3 h at 130° C. and 50-200 mbarand the ethanol liberated is distilled off. 125 g of product areobtained.

Example 20

Preparation of C₆H₅—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

91 g of Cl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 50 g of thiobenzoic acid and 250g of dry DMF are combined under inert gas at 25° C. in a flask. 36.5 gof triethylamine are added dropwise to the mixture, and the solutionobtained is stirred for 120 min at room temperature and then for 240 minat 140° C. Cooling is effected and 300 ml of dry toluene are added. Theprecipitate is separated off by filtration and washed with toluene, andthe filtrate is as far as possible freed from the solvent on a rotaryevaporator. 142 g of a viscous, dark red product are obtained.

Example 21

Preparation of C₆H₅—C(O)—S—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N

91 g of Cl—CH₂—CH₂—CH₂—Si(O—CH₂—CH₂)₃N, 50 g of thiobenzoic acid and 300g of dry toluene are combined under inert gas at 25° C. in a flask. 36.5g of triethylamine are added dropwise to the mixture, and the solutionobtained is stirred for 120 min at room temperature and then for 240 minat 108° C. The suspension is cooled, the precipitate is separated off byfiltration and washed with toluene, and the filtrate is freed from thesolvent on a rotary evaporator. 127 g of a viscous, dark red product areobtained.

All references cited herein are fully incorporated by reference. Havingnow fully described the invention, it will be understood by those ofskill in the art that the invention may be practiced within a wide andequivalent range of conditions, parameters and the like, withoutaffecting the spirit or scope of the invention or any embodimentthereof.

1. An organosilicon compound of the general formula (I),Q—[S—G—Si(—O—CX¹X²—CX¹X³—)₃N]  (I) in which Q is SiX⁴ _(3−t)X⁵t—, wheret=0, 1 or 2, Y—C(═O)—Z—C(═O)—, Y—C(═S)—Z—C(═S)—, Y—C(═NR)—Z—C(═NR)—,Y—C(═O)—, Y—C(═S)—, Y—C(═NR)—, Y—S(═O)—, Y—S(═O)₂—, (X⁶) (X⁷)P(═S)—,(X⁶) (X⁷)P(═O)—, X⁸—C(═O)—, R—C(═S)—, R—C(═NR)—, R—S—C(═NR)—,R—S—C(═O)—, R—S—C(═S)—, (X⁹)₂N—C(═O)—, (X⁹)₂N—C(═S)—, R—NR—C(═NR)—,(X⁸)₂N—C(═O)—, (X⁸)₂N—C(═S)—, (X⁸)HN—C(═O)—, (X⁸)NH—C(═S)—, R—O—C(═O)—,X⁹—O—C(═S)—, R—O—C(═NR)—, R—S(═O)—, R—S(═O)₂—, R—O—S(═O)₂—,R—NR—S(═O)₂—, R—S—S(═O)₂—, R—S—S(═O)—, R—O—S(═O)—, R—NR—S(═O)—,(R—S—)₂P(═O)—, (R—S—)₂P(═S)—, (R—NR—)₂P(═S)—, (R—NR—)₂P(═O)—,R—(R—S—)P(═O)—, R—(R—O—)P(═O)—, R—(R—S—)P(═S)—, R—(R—O—)P(═S)—,R—(R—NR—)P(═O)—, R—(R—NR—)P(═S)—, (R—NR—)(R—S—)P(═O)—,(R—O—)(R—NR—)P(═O)—, (R—O—)(R—S—)P(═O)—, (R—O—)(R—S—)P(═S)—,(R—NR—)(R—S—)P(═S)—, (R—O—)(R—NR—)P(═S)—, (R—O—)(Y)P(═O)—,(R—O—)(Y)P(═S)—, (R—S—)(Y)P(═O)—, (R—S—)(Y)P(═S)—, (R—NR—)(Y)P(═O)—,(R—NR—)(Y)P(═S)—, R—(Y)P(═O)—, R—(Y)P(═S)—, Y₂P(═O)—, Y₂P(═S) —orY₂P(NR)—, R are identical or different and are hydrogen (H), astraight-chain, cyclic or branched, substituted or unsubstituted,saturated or unsaturated monovalent (C₁-C₂₄)-hydrocarbon chain, anunsubstituted or —NH₂, HS—, Cl— or Br-substituted (C₆-C₂₄)-aryl group oran unsubstituted or —NH₂, HS—, Cl— or Br-substituted (C₇-C₂₄)-aralkylgroup, Y are identical or different and are[—S—G—Si(—O—CX¹X²—CX¹X³—)₃N], G are identical or different and when Q isC₆H₅—C(═O)— G is a straight-chain, cyclic or branched, substituted orunsubstituted, saturated or unsaturated divalent (C₃-C₃₀)-hydrocarbonchain; optionally, the hydrocarbon chains may contain unsaturatedmoieties or may be substituted by them, and for all other Q, G is astraight-chain, cyclic or branched, substituted or unsubstituted,saturated or unsaturated divalent (C₁-C₃₀)-hydrocarbon chain;optionally, the hydrocarbon chains may contain unsaturated moieties ormay be substituted by them, Z is a straight-chain, cyclic or branched,substituted or unsubstituted, saturated or unsaturated divalent(C₁-C₂₄)-hydrocarbon chain; optionally, the hydrocarbon chains maycontain unsaturated moieties or may be substituted by them, or is adivalent, aliphatic or aromatic, saturated or unsaturated hydrocarbonchain functionalized with at least two NH groups, X¹, X² and X³, in eachcase independently of one another, denote hydrogen (—H), (C₁-C₁₆)-alkylor aryl, X⁴ and X⁵, in each case independently of one another, denotehydrogen (—H), a straight-chain, cyclic or branched, substituted orunsubstituted, saturated or unsaturated monovalent (C₁-C₂₄)-hydrocarbonchain, a (C₁-C₈)-alkoxy group, an aryl group, an alkylether groupO—(CR^(I) ₂—CR^(I) ₂)—O-Alk or alkylpolyether group O—(CR^(I) ₂—CR^(I)₂O)_(y)-Alk, where y=2-25, R^(I), independently of one another, are H oran alkyl group, Alk is a linear or branched, saturated or unsaturatedalkyl chain having 1-30 carbon atoms (C₁-C₃₀), an aralkyl group,ahalogen, a radical Alk-(COO), or Y, X⁶ and X⁷, in each caseindependently of one another, denote hydrogen (—H), —OH, —SH, astraight-chain, cyclic or branched, substituted or unsubstituted,saturated or unsaturated monovalent (C₁-C₂₄)-hydrocarbon chain, a(C₄-C₂₄)-alkoxy group, an aryl group, an alkylether group O—(CR^(I)₂—CR^(I) ₂)—O-Alk or alkylpolyether group O—(CR^(I) ₂—CR^(I)₂O)_(y)-Alk, an aralkyl group, a halogen or a radical Alk-(COO), X⁸ areidentical or different and denote hydrogen (H), a straight-chain, cyclicor branched, substituted or unsubstituted, saturated or unsaturatedmonovalent (C₂-C₂₄)-hydrocarbon chain, an —NH₂, HS—, Cl—, Br—substituted (C₆-C₂₄)-aryl group, an unsubstituted (C₆-C₂₄)-aryl group oran unsubstituted or —NH₂, HS—, Cl— or Br-substituted (C₇-C₂₄)-aralkylgroup, X⁹ are identical or different and denote hydrogen (H), astraight-chain, cyclic or branched, substituted or unsubstituted,saturated or unsaturated monovalent (C₄-C₂₄)-hydrocarbon chain, an —NH2,HS—, Cl— or Br-substituted (C₆-C₂₄)-aryl group, an unsubstituted(C₇-C₂₄)-aryl group or an unsubstituted or —NH₂, HS—, Cl— orBr-substituted (C₇-C₂₄)-aralkyl group.
 2. The organosilicon compound ofclaim 1, wherein said organosilicon compound is applied to or mixed withan inert organic or inorganic support or is subjected to a preliminaryreaction with an organic or inorganic support.
 3. A process for thepreparation of an organosilicon compound according to claim 1,comprising reacting at least one organosilicon compound of the generalformula (II),X¹⁰[S—G—Si(—O—CX¹X²—CX¹X³—)₃N]  (II) in which R, Y, Z, X⁴, X⁵, X⁶, X⁷,X⁸, X⁹ and t have the same meanings as in formula (I) and X¹⁰ is H,alkali metal, alkaline earth metal or ammonium cation, with at least onecompound selected from the group consisting of

Y—C(═O)—O—C(═O)—Y, Y—C(═S)—O—C(═S)—Y, Y—C(═NR)—O—C(═NR)—Y,Y—C(═O)—S—C(═O)—Y, Y—C(═S)—S—C(═S)—Y, Y—C(═NR)—S—C(═NR)—Y,Y—S(═O)—O—S(═O)—Y, Y—S(═O)₂—O—S(═O)₂—Y, X⁸—C(═O)—O—C(═O)—X⁸, X⁸—C(═O)—S—C(═O)—X⁸, R—C(═S)—O—C(═O)—R, R—C(═S)—S—C(═O)—R,R—S—C(═O)—O—C(═O)—S—R, R—S—C(═O)—S—C(═O)—S—R, R—S—C(═S)—O—C(═S)—S—R,R—S—C(═S)—S—C(═S)—S—R, R—O—C(═O)—O—C(═O)—OR, R—O—C(═O)—S—C(═O)—OR,R—O—C(═S)—O—C(═S)—OR, R—O—C(═S)—S—C(═S)—OR, R—S(═O)—O—S(═O)—R,R—S(═O)—S—S(═O)—R, R—O—S(═O)—O—S(═O)—O—R, R—O—S(═O)—S—S(═O)—O—R,R—O—S(═S)—O—S(═S)—O—R, R—O—S(═S)—S—S(═S)—O—R, R—S—S(═O)—O—S(═O)—S—R,R—S—S(═O)—S—S(═O)—S—R, R—S—S(═S)—O—S(═S)—S—R, R—S—S(═S)—S—S(═S)—S—R,R—S(═O)₂—O—S(═O)₂—R, R—S(═O)₂—S—S(═O)₂—R, R—S(═S)₂—O—S(═S)₂—R,R—S(═S)₂—S—S(═S)₂—R, R—O—S(═O)₂—O—S(═O)₂—O—R, R—O—S(═O)₂—S—S(═O)₂—O—R,R—O—S(═S)₂—O—S(═S)₂—O—R, R—O—S(═S)₂—S—S(═S)₂—O—R,R—S—S(═O)₂—O—S(═O)₂—S—R, R—S—S(═O)₂—S—S(═O)₂—S—R,R—S—S(═S)₂—O—S(═S)₂—S—R, R—S—S(═S)₂—S—S(═S)₂—S—R, SiX⁴ _(s)X⁵_(2−s)(Y)—S—SiX⁴ _(s)X⁵ _(2−s)(Y), SiX⁴ _(3−t)X⁵ _(t)—S—Six⁴ _(3−t)—X⁵_(t), Y₂SiX⁴—S—SiX⁵Y₂, Y₂P(═O)—S—P(═O)Y₂, Y₂P(═S)—S—P(═S)Y₂, SiX⁴_(3−t)—X⁵ _(t)-halogen, halogen-C(═O)—Z—C(═O)-halogen,halogen-C(═S)—Z—C(═S)-halogen, halogen-C(═NR)—Z—C(═NR)-halogen,Y—C(═O)—Z—C(═O)-halogen, Y—C(═S)—Z—C(═S)-halogen,Y—C(═NR)—Z—C(═NR)-halogen, halogen-C(═O)-halogen, halogen-C(═S)-halogen,halogen-C(═NR)-halogen, halogen-S(═O)-halogen, halogen-S(═O)₂-halogen,Y—C(═O)-halogen, Y—C(═S)-halogen, Y—C(═NR)-halogen, Y—S(═O)-halogen,Y—S(═O)₂-halogen, (X⁶)(X⁷)P(═S)-halogen, (X⁶)(X⁷)P(═O)-halogen,X⁸—C(═O)-halogen, R—C(═S)-halogen, R—C(═NR)-halogen, R—S—C(═NR)-halogen,R—S—C(═O)-halogen, R—S—C(═S)-halogen, (X⁹)₂N—C(═O)-halogen,(X⁹)₂N—C(═S)-halogen, R—NR—C(═NR)-halogen, R—O—C(═O)-halogen,X⁹—O—C(═S)-halogen, R—O—C(═NR)-halogen, R—S(═O)-halogen,R—S(═O)₂-halogen, R—O—S(═O)₂-halogen, R—NR—S(═O)₂-halogen,R—S—S(═O)₂-halogen, R—S—S(═O)-halogen, R—O—S(═O)-halogen,R—NR—S(═O)-halogen, (R—S—)₂P(═O)-halogen, (R—S—)₂P(═S)-halogen,(R—NR—)₂P(═S)-halogen, (R—NR—)₂P(═O)-halogen, R—(R—S—)P(═O)-halogen,R—(R—O—)P(═O)-halogen, R—(R—S—)P(═S)-halogen, R—(R—O—)P(═S)-halogen,R—(R—NR—)P(═O)-halogen, R—(R—NR—)P(═S)-halogen,(R—NR—)(R—S—)P(═O)-halogen, (R—O—)(R—NR—)P(═O)-halogen,(R—O—)(R—S—)P(═O)-halogen, (R—O—)(R—S—)P(═S)-halogen,(R—NR—)(R—S—)P(═S)-halogen, (R—O—)(R—NR—)P(═S)-halogen,(R—O—)P(═O)(O—R)₂, (R—O—)P(═S)(O—R)₂, (R—S—)P(═O)(O—R)₂,(R—S—)P(═S)(O—R)₂₁ (R—NR—)P(═O)(O—R)₂, (R—NR—)P(═S)(O—R)₂,R—P(═O)(O—R)₂, R—P(═S)(O—R)₂, (R—O—)(Y)P(═O)-halogen,(R—O—)(Y)P(═S)-halogen, (R—S—)(Y)P(═O)-halogen, (R—S—)(Y)P(═S)-halogen,(R—NR—)(Y)P(═O)-halogen, (R—NR—)(Y)P(═S)-halogen, R—(Y)P(═O)-halogen,R—(Y)P(═S)-halogen, P(═O)(halogen)₃, P(═S)(halogen)₃, P(NR)(halogen)₃,Y—P(═O)(halogen)₂, Y—P(═S)(halogen)₂, Y—P(NR)(halogen)₂,Y₂P(═O)-halogen, Y₂P(═S)-halogen, Y₂P(NR)-halogen, SiX⁴ _(3−t)X⁵_(t)—O—R, SiX⁴ ₂—(O—R)₂, SiX⁵—(O—R)₃, R—O—C(═O)—Z—C(═O)—O—R,R—O—C(═S)—Z—C(═S)—O—R, R—O—C(═NR)—Z—C(═NR)—O—R,halogen-C(═O)—Z—C(═O)—O—R, halogen-C(═S)—Z—C(═S)—O—R,halogen-C(═NR)—Z—C(═NR)—O—R, R—O—C(═O)—Z—C(═O)—O—R,R—O—C(═S)—Z—C(═S)—O—R, R—O—C(═NR)—Z—C(═NR)—O—R, Y—C(═O)—Z—C(═O)—O—R,Y—C(═S)—Z—C(═S)—O—R, Y—C(═NR)—Z—C(═NR)—O—R, halogen-C(═O)—O—R,halogen-C(═S)—O—R, halogen-C(═NR)—O—R, halogen-S(═O)—O—R,halogen-S(═O)₂—O—R, R—O—C(═O)—O—R, R—O—C(═S)—O—R, R—O—C(═NR)—O—R,R—O—S(═O)—O—R, R—O—S(═O)₂—O—R, Y—C(═O)—O—R, Y—C(═S)—O—R, Y—C(═NR)—O—R,Y—S(═O)—O—R, Y—S(═O)₂—O—R, (X⁶)(X⁷)P(═S)—O—R, (X⁶)(X⁷)P(═O)—O—R,X⁸—C(═O)—O—R, R—C(═S)—O—R, R—C(═NR)—O—R, R—S—C(═NR)—O—R, R—S—C(═O)—O—R,R—S—C(═S)—O—R, (X⁹)₂N—C(═O)—O—R, (X⁹)₂N—C(═S)—O—R, R—NR—C(═NR)—O—R,X⁹—O—C(═S)—O—R, R—S(═O)—O—R, R—S(═O)₂—O—R, R—NR—S(═O)₂—O—R,R—S—S(═O)₂—O—R, R—S—S(═O)—O—R, R—NR—S(═O)—O—R, (R—NR—)₂P(═S)—O—R,(R—NR—)₂P(═O)—O—R, R—(R—S—)P(═O)—O—R, R—(R—S—)P(═S)—O—R,R—(R—NR—)P(═O)—O—R, R—(R—NR—)P(═S)—O—R, (R—NR—)(R—S—)P(═O)—O—R,(R—O—)(R—NR—)P(═O)—O—R, (R—NR—)(R—S—)P(═S)—O—R, (R—S—)P(═O)(O—R)₂,(R—S—)P(═S)(O—R)₂, (R—NR—)P(═O)(O—R)₂, (R—NR—)P(═S)(O—R)₂,R—P(═O)(O—R)₂, R—P(═S)(O—R)₂, (R—S—)(Y)P(═O)—O—R, (R—S—)(Y)P(═S)—O—R,(R—NR—)(Y)P(═O)—O—R, (R—NR—) (Y)P(═S)—O—R, R—(Y)P(═O)—O—R,R—(Y)P(═S)—O—R, P(═O)(O—R)₃, P(═S)(O—R)₃, P(NR)(O—R)₃, Y—P(═O)(O—R)₂,Y—P(═S)(O—R)₂, Y—P(NR)(O—R)₂, Y₂P(═O)—O—R, Y₂P(═S)—O—R or Y₂P(NR)—O—R,SiX⁴ _(3−t)X⁵ _(t)—S—R, SiX⁴ ₂—(S—R)₂, SiX⁵—(S—R)₃,R—O—C(═O)—Z—C(═O)—S—R, R—O—C(═S)—Z—C(═S)—S—R, R—O—C(═NR)—Z—C(═NR)—S—R,halogen-C(═O)—Z—C(═O)—S—R, halogen-C(═S)—Z—C(═S)—S—R,halogen-C(═NR)—Z—C(═NR)—S—R, R—S—C(═O)—Z—C(═O)—S—R,R—S—C(═S)—Z—C(═S)—S—R, R—S—C(═NR)—Z—C(═NR)—S—R, Y—C(═O)—Z—C(═O)—S—R,Y—C(═S)—Z—C(═S)—S—R, Y—C(═NR)—Z—C(═NR)—S—R, halogen-C(═O) —S—R,halogen-C(═S)—S—R, halogen-C(═NR)—S—R, halogen-S(═O)—S—R,halogen-S(═O)₂—S—R, R—S—C(═O)—S—R, R—S—C(═S)—S—R, R—S—C(═NR)—S—R,R—S—S(═O)—S—R, R—S—S(═O)₂—S—R, Y—C(═O)—S—R, Y—C(═S)—S—R, Y—C(═NR)—S—R,Y—S(═O)—S—R, Y—S(═O)₂—S—R, (X⁶)(X⁷)P(═S)—S—R, (X⁶)(X⁷)P(═O)—S—R,X⁸—C(═O)—S—R, R—C(═S)—S—R, R—C(═NR)—S—R, (X⁹)₂N—C(═O)—S—R,(X⁹)₂N—C(═S)—S—R, R—NR—C(═NR)—S—R, X⁹—O—C(═S)—S—R, R—S(═O)—S—R,—R—S(═O)₂—S—R, R—NR—S(═O)₂—S—R, R—NR—S(═O)—S—R, (R—NR—)₂P(═S)—S—R,(R—NR—)₂P(═O)—S—R, R—(R—O—)P(═O)—S—R, R—(R—O—)P(═S)—S—R,R—(R—NR—)P(═O)—S—R, R—(R—NR—)P(═S)—S—R, (R—O—)(R—NR—)P(═O)—S—R,(R—O—)(R—NR—)P(═S)—S—R, (R—O—)P(═O)(S—R)₂, (R—O—)P(═S)(S—R)₂,(R—S—)P(═O)(S—R)₂, (R—NR—)P(═O)(S—R)₂, (R—NR—)P(═S)(S—R)₂,R—P(═O)(S—R)₂, R—P(═S)(S—R)₂, (R—O—)(Y)P(═O)—S—R, (R—O—)(Y)P(═S)—S—R,(R—NR—)(Y)P(═O)—S—R, (R—NR—)(Y)P(═S)—S—R, R—(Y)P(═O)—S—R,R—(Y)P(═S)—S—R, P(═O)(S—R)₃, P(═S)(S—R)₃, P(NR)(S—R)₃, Y—P(═O)(S—R)₂,Y—P(═S)(S—R)₂, Y—P(NR)(S—R)₂, Y₂P(═O)—S—R, Y₂P(═S)—S—R or Y₂P(NR)—S—R,in which R. Y, Z, X⁴, X⁵, X⁶, X⁷, X⁸, X⁹ and t have the same meanings informula (I) and s is 1 or
 2. 4. A process for the preparation of theorganosilicon compound of claim 1, wherein a compound of the generalformula (IV),Q(—SH)  (IV) in which Q has the same meaning as in formula (I), issubjected to an addition reaction with an organosilicon compoundcontaining at least one double bond (═) and of the general formula (V),CX¹X²═CX²—G¹—Si(O—CX¹X²—CX¹X³)₃N  (V) in which X¹, X² and X³ have thesame meanings as in formula (I), —CX¹X²—CHX²—G¹ or HCX¹X²—CX₂(—)—G¹being G.
 5. A process for the preparation of the organosilicon compoundof claim 1, comprising reacting a compound of the general formula (VI),Q(—S—X¹⁰)  (VI) in which Q has the.same meaning as in formula (I) andX¹⁰ has the same meaning as in formula (II), with a compound of thegeneral formula (VII),halogen-G—Si(O—CX¹X²—CX¹X³)₃N  (VII) in which X¹, X², X³ and G have thesame meanings as in formula (I).
 6. A process for the preparation of theorganosilicon compound of claim 1, comprising reacting at least onesilane of the general formulae VIII-XI,Q—[S—G—Si(alkoxy)₃]  (VIII)(alkoxy)₃Si—G—S—C(═O)—Z—C(═O)—S—G—Si(alkoxy)₃   (IX)(alkoxy)₃Si—G—S—C(═S)—Z—C(═S)—S—G—Si(alkoxy)₃   (X)(alkoxy)₃Si—G—S—C(═NR)—Z—C(═NR)—S—G—Si(alkoxy)₃   (XI) in which G, Q,and Z have the same meanings as in formula (I) and alkoxy, independentlyof one another, are (C₁-C₂₄)-alkoxy, with a compound of the generalformula XII,(HO—CX¹X₂—CX¹X³—)₃N  (XII) in which X¹, X², and X³ have the samemeanings as in formula (I), with the elimination of (alkoxy)-H, and theseparation of (alkoxy)-H from the reaction mixture.
 7. A compositioncomprising at least one organosilicon compound according to claim
 1. 8.The composition of claim 7, wherein said composition is a rubbermixture, comprising, in addition to said organosilicon compound, rubber,and filler.
 9. The composition of claim 8, wherein said rubber mixtureis part of a moulding.
 10. The composition of claim 8, wherein saidrubber mixture is used in a pneumatic tire, tire tread,rubber-containing tire constituent, cable sheath, hose, drive belt,conveyor belt, roll covering, tire, shoe sole, sealing ring or dampingelement.